


We Had a Marvelous Time Ruining Everything

by witchesandwaves



Category: Gilmore Girls
Genre: AU, Angst, F/F, F/M, Gilmore Girls: A Year in the Life Fix-It, Not Gilmore Girls: A Year in the Life Compliant, Slow Burn
Language: English
Status: In-Progress
Published: 2020-09-10
Updated: 2020-12-27
Packaged: 2021-03-06 18:20:55
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 11
Words: 22,338
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26383276
Author URL: https://archiveofourown.org/users/witchesandwaves/pseuds/witchesandwaves
Summary: It's Lorelai's wedding week, and Rory may have just lost her job, her boyfriend, and her apartment all in one day. Determined not to let her quarter-life crisis get in the way of Lorelai's excitement, Rory confides in an old flame--and realizes that her feelings may not entirely have gone away.AU, set 5 years after the season 7 finale. Everything in the show is canon, except that Lane never got pregnant and divorced Zach after about a year. A Year in the Life never happened, because it was bad. And even though it’s only 5 years after season 7 ended, it’s 2019, because it just is.
Relationships: Luke Danes/Lorelai Gilmore, Paris Geller/Lane Kim, Rory Gilmore/Jess Mariano
Comments: 43
Kudos: 89





	1. In Which Rory Gilmore is Not Having the Best Day

Rory wasn’t sure where it had all gone wrong. 

Wrong might not be the right word, but it sure felt like it tonight. Driving her Prius from Boston to Stars Hollow and feeling like she was somehow minus a job, a boyfriend, and an apartment, all in one night; the last time she could remember losing two out of three, she’d at least had Paris, who wasn’t always perfect but who loved her, flaws and all, the way only a best friend can, and who’d commiserated with her and ordered more Chinese food than they could finish in two lifetimes (not for lack of trying, of course), and insulted the general existence of men with her until she started to feel back to resembling human. But Paris couldn’t have been there for Rory tonight, even if she’d wanted to, because she was on a 48-hour shift as part of her residency, Grey’s Anatomy-style, although Paris would rant about the show’s inaccuracies every time Rory so much as breathed near a reference to ferry boats or cupcakes or “picking” anything. And although, if Rory had called her, if she’d really needed her, there was at least a 50% chance Paris would have told her attending physician they could suck it, Rory wasn’t going to do that to her. It wasn’t until she’d gotten in the car, on the way home, to Stars Hollow, to talk to her mother about it, that she’d realized she couldn’t talk to Lorelai either—because Lorelai, finally, finally, was getting married, and Rory would rather endure a thousand Paris/Grey’s Anatomy rants than get in the way of Lorelai’s happiness this week. 

Rory took in a deep breath and let it out. It wasn’t a long drive, and as she cranked up the music (Queen, because she wasn’t the kind of girl who cried in her car to depressing breakup music, because where was the challenge in that, she cried in her car to defiantly happy music) she found herself wishing it was longer; long enough, maybe, to get what had just happened—with her job, her apartment, her boyfriend, her life—out of her head, at least for this week.

It had been a bad day, a bad day in a string of bad days. Rory’d been working for Hugo Gray again, the millennial news site founder who’d hired her straight out of Yale to cover the Obama campaign for him, the first guy who’d given her a real shot as a journalist (because Chilton didn’t count, no matter how much she’d thought it did at the time, and the Yale Daily News didn’t count, despite how much Doyle had wanted it to at the time—it was true that the market for lacrosse game commentary and chamber music reviews dried up pretty quickly the second you left college, and because of course, that trap Rory had walked into with Mitchum didn’t count, since he’d never meant to give her a real shot in the first place, just to play with her in that disturbing way rich people always seemed to play with those around them--she’d seen it with Logan, with Colin and Finn, even with Emily and Richard at times, although with them at least she’d acknowledge that they had intentions that, if not good exactly, were intended to benefit their family in the way that they had been raised to see as right.) and it had been going well at first, she thought; grad school had given her a new perspective on her writing, and on journalism as a whole. It was dying, was the perspective, but she was among the few actively working to preserve the profession, to fight against the rising tide of punditry and the ridiculous, hated cries of “fake news,” to tell the truth, even if it wasn’t clickbait, even if it didn’t drive traffic the way a listicle might. And Hugo understood that, as well; he was a rare boss in that his primary motivation for his news site wasn’t the highest profits, the most clicks, the most ad revenue, but the most accurate, vetted reporting; the most motivated reporters—young and underpaid, to be sure, but ones who cared. Like Rory. She felt like she fit there, at the Whistleblower, with its community office space feel, idealistic staff, and truly horrific coffee. 

Until today.

She squeezed her eyes shut for just a second, remembered she was driving, and wrenched them open immediately. She wasn’t thinking about this. Not now.

Except every time she lost control of her thoughts for a second they drifted back to the way Hugo had looked at her today, like he genuinely had thought she was better than this, and like he was just now realizing that she wasn’t. And maybe she’d realized it too. And maybe that was the worst part. 

“Another One Bites the Dust” started playing, and Rory aggressively pressed the skip button. “Somebody to Love” was up next, and Rory left it on, because even if it wasn’t necessarily the best premise to cheer her up, it at least wasn’t mocking her too much. Until she let her mind jerk back towards Logan, and what else had happened today, and honestly, it had never really gone away. So she let the song play, and let herself cry, really cry, ugly crying, and through her ugly crying wondering aloud whether there wasn’t newer music out that she could cry better to, wondering whether she should really consider mixing up her Spotify playlists.

“I mean, millennials can’t be the only ones who need to cry in their cars, can they?” she sobbed, her vision blurring and then clearing as she swiped the tears away from her eyes. She remembered the last time she’d cried like this, out of control like this, in the school psychologist’s office at Yale, in one of her school-mandated therapy sessions after she’d taken time off. It wasn’t like she hadn’t cried since then, of course she had, but the raw, tissue-devouring sobs she’d let out then she really hadn’t seen in awhile. She tried to distract herself from the pain of today by thinking back to that session—when she’d only just recently forced herself back on track after completely losing her mind for half a year—and Logan had told her he loved her for the first time, at the exact wrong time. She’d wondered, secretly, if the timing of that, that first time he’d said it to her, had doomed them somehow, had meant that he’d never really feel for her what she needed when she needed it, and then half a second later had convinced herself to stop being crazy, that this was the kind of weird, obsessive thinking she had to stop in its tracks before it took over and she was saying it, out loud, to Logan. It wasn’t the first time she’d wondered it; after the first time she’d told him she loved him, which was extremely regrettably after he’d given her the ridiculously extravagant pink Birkin bag (she cringed every time she thought about it), she’d thought, at least in part (even though she told him she didn’t care, because she was a cool girl, wasn’t she) that he’d say it back. And he hadn’t, and she’d told him it was fine, because it was, wasn’t it?

And it wasn’t like she had the best track record, in general, with boys telling her they loved her. More like the worst track record of all time. Like when Dean had broken up with her because she couldn’t say it back. Or when Jess had said it and then run away immediately afterwards.  
Maybe she was just the kind of girl who could only be loved at inconvenient times, or badly, or weirdly. She was the common denominator in these situations, wasn’t she? 

Her sobs, which had intensified when she’d recalled her previous crying fit, were subsiding, at least to some degree. Analyzing things normally helped, when she felt like she was going to spin out of control. Pro/con lists, in particular. Absently, she began to make one, out loud, about the current state of her life, hoping it would come out in such a way that made her feel even a little bit better, but worrying that it wouldn’t.  
“Pros. I’m alive. That’s a good one. Um. My mom is getting married, finally, to Luke, finally, and they’re in love. And they love me. That’s a good one, too.” She paused a moment, considering. “Lane. Paris. I have two best friends, actually three best friends, because my mom is, well, my original best friend, and my other two best friends are alive and happy and they love me. Even if all of us are crazy sometimes.” She laughed, grabbing tissues from the floor of her car to swipe at her face with. Crying pretty was tough. 

“Journalism. I have my degree, from Yale, with is nothing to sneeze at. What a ridiculous expression, sneeze at. I wonder who invented it?” She imagined, briefly, the nonsensical and increasingly frustrating conversation that would develop if she brought that up at Friday night dinner. Or would have, if they still had Friday night dinners.

“And I have my graduate degree. Which is good. And I have books. Those still exist. And news, even if it’s hated by half the country and our current administration.” She was getting off topic.

“Lucy and Olivia. I have them, too, even I don’t get to see them all the time.” They’d moved to New York right after graduation, as planned, and were still there, sticking it out, working on their respective crafts. She got to see them at least once of twice a year when they visited back and forth, and being around them was a refreshing confirmation that she didn’t need to have it all figured out, not yet, at least.

But she had, almost. This morning. Had it all figured out. And now none of it was.

“Cons.” She took a deep breath. “I don’t know if I still have a job. I don’t know what’s going to happen with Logan. And since I live with Logan, and since he pays for most of the apartment, I don’t know where I’m going to live.” She stated it as devoid of emotion as she could, breathing through it, and oddly enough, hearing those three things laid out baldly, just like that, in the stale, tear-filled air of her Prius, she somehow felt oddly better.

“Pro,” she said, feeling bolder all of the sudden. “I’m going to get through this, because I’m Rory freaking Gilmore.” And then, bolder still, chastising her inner voice that kept her from saying what she wanted to say, when she most needed to say it and hear it, “I’m Rory fucking Gilmore, and I’m going to figure this out.”


	2. In Which Rory Takes a Detour

**Notes for the Chapter:**

> Thank you so much to everyone reading so far! I'm having a lot of fun writing this, both because I really like the idea of giving the Gilmore Girls a different ending and because, well, it's a great distraction from the mess that is 2020. I have a lot of ideas about where everything is going, and I hope you like it :)

Rory fucking Gilmore was still going to need a minute, she realized as she drove past Luke’s diner, meaning that she was now uncomfortably close to her mom and Luke’s house. She’d definitely calmed down after her strangely helpful pro/con list (that wasn’t actually very helpful at all if you thought about it enough, which was why she wasn’t going to), but she was still sniffling, and her eyes were still red, and if she tried to play it off like she was getting over a cold she’d probably be banished to Hartford for the duration of the wedding, possibly only being allowed to Skype in for the ceremony. Maybe April could carry her phone down the aisle with Rory on Facetime, insisting loudly that she wasn’t contagious, while April recited statistics about the transmissibility of the common cold. Lorelai hated being sick, and her complaining about being sick made Luke crazy, and neither could be permitted this week, when they’d waited years, no, over a decade, for this to finally happen. 

So she was going to need a minute.

In a flash of nostalgia, she almost started driving to Lane’s old apartment, somehow thinking that she’d find her there to talk things out, forgetting, for just a moment, that Lane didn’t live here anymore, and that she’d seen her in Boston just last week. Lane didn’t love Boston; she’d much rather be somewhere less preppy and filled with fewer undergrad students and a better music scene, but on a trip to visit Rory about two years ago she’d seen a flier for a band needing a drummer, and the rest was history. Well, it wasn’t history—it took Lane awhile to get over her trust issues from her old band, which undoubtedly made good music together but had fallen apart from self-sabotage and jealousy and then reunited, only to then separate for good after her divorce. She was doing well, though, better than Rory had ever seen her—she was becoming more confident in herself and her independence, and the new band, although slightly more emo than Lane liked, had been welcoming and a lot of fun. 

Lane would be there for the wedding, of course, which wasn’t until Saturday night, and since it was only Sunday, that meant six whole days until Lane could sit for a vent session. Sure, Rory could have seen her tonight instead of fleeing Boston like Matt Damon with his sights on an Oscar-bait role, but the overwhelming urge to just leave, to get out of there, had overtaken her completely. Like with Paris, it was probably better this way—Lane had band practice tonight anyways, and she was always in such a good mood afterwards that Rory would feel bad bringing her down, and she had probably gone out for burgers afterwards anyways.

Why are you so down, Ace? She could almost hear Logan’s voice in her head. It’s a party, come on, everyone’s having a good time! Why don’t you relax and have a drink, you’ll feel better, I promise. 

She shook her head to clear it. Nope. Not going down that road again, not in the wake of a solid pro/con list. She wrenched the wheel to the right and away from Lane’s house in what in her imagination was a fit of speed, but was probably only about five over the absurdly low Stars Hollow speed limit. Rory was always a careful driver (You won’t go ten over the limit but you’ll steal a boat with me, huh Ace?), but it was her mind that felt like it was out of control. So when she ended up back in front of Luke’s, she almost laughed. When she was younger, whenever she hadn’t known where to go, whenever she was in a good mood, or a bad mood, or an “I need fries in the next ten seconds or I will burn Chilton to the ground” mood, she ended up at Luke’s. 

It was closed, of course, since it was nearly midnight and also because Luke had promised Lorelai he’d close down for the week of the wedding after a heated, extensive argument about whether a wedding day or a wedding week was the correct amount of time for all eyes to be focused on the happy couple (Luke insisting that he did not want any eyes on him at all, and that even his nemesis Taylor had referred to it as their “special day” in passing, Lorelai grandiosely and half-jokingly stating that the town was lucky she wasn’t asking for a “wedding month”) that was only resolved when Rory pointed out that this same argument had taken place on Sex and the City, and Luke was so disgusted he’d caved immediately. 

Rory really didn’t know how she’d get through this week dealing with the Logan situation (and the job situation, and the apartment situation), but a week in Stars Hollow without Luke’s seemed even worse at this exact second, somehow. Rationally, she knew that Luke would be at her mother’s house, and happy to make her anything she asked for, but it wasn’t the same. She wanted Luke’s, and she wanted it now, and nothing else was going to make her feel better.

As she parked and hopped out of her Prius, slamming the door shut loud enough to satisfy her mood but softly enough that Taylor wouldn’t run out of his house threatening a noise complaint, Rory recognized exactly how childish and petty she was being, ignored it, and strode up to the door. She stretched onto her toes, feeling along the top of the doorframe for the key that she knew Luke kept there for emergencies (well, Luke didn’t keep it there, Lorelai did, and Luke would probably set off on a rant about being too trusting of the secretly nefarious citizens of Stars Hollow if he knew). She didn’t feel anything, so she stretched further, reaching over into the corner, when the door of the seemingly dark and empty diner was jerked open and she stumbled back, almost losing her balance. Strong arms grasped hers and righted her, and she found herself too close, way too close, to the dark brown eyes of the best and worst person she could possibly run into right now.

“Hey, Rory,” said Jess.


	3. In Which Rory Turns the Tables

**Summary for the Chapter:**

> Rory runs into someone she didn't expect to see, and it brings back memories she can't think about right now.

**Notes for the Chapter:**

> I just want to say thank you so much to everyone reading, and also that we're going to get pretty angsty in this chapter, so buckle up (and please don't hate me! This thing is going to be long, but there'll be an HEA, I promise)...

Rory froze, staring at Jess, irrationally hoping that she was either hallucinating or that she would, in the next few seconds, spontaneously develop the ability to become invisible. He was grinning at her, an expression she’d only ever seen on his face when she was around: a hint of a smirk but amused instead of ironic. It made her feel for just a moment like she was seventeen again, and she’d found someone smart, someone different, someone who got her on a level that Dean hadn’t. 

And then she abruptly realized that not only was she not seventeen anymore (she was TEN YEARS OLDER, how the hell had that happened), but also that she was still staring, and that his arms hadn’t left hers. She pulled away, surreptitiously wiping her eyes and adjusting the sleeves of her brown sweater (why couldn’t she have had an emotional breakdown and run back to Stars Hollow wearing, say, a cute blazer, or a dress? Not that it mattered what Jess saw her in, not even a little bit), trying to act nonchalant and likely failing miserably. She knew her eyes still had to be red, and she tried to hide it by looking back over her shoulder and pretending to be absorbed in staring back at the town square. 

“So, did you not take Breaking and Entering 101 at Yale?” Jess asked her, still grinning.

“I was going to,” said Rory, who still felt off-balance even though she was clearly standing on her own two feet again, “But it conflicted with my Intro to Falling Over seminar, so I was out of luck.”

“Still managed to sneak in Grand Theft Boating for Beginners, though, or so I hear.”

“What?” she glared at him, caught off guard and embarrassed, the way she always felt when someone dragged that up again. “I never told you about the boat,” she said. She’d have remembered that conversation, she was sure.

“Luke told me,” Jess said, leaning against the doorframe. 

“No one was supposed to know! We had it expunged from my record a few years ago. My grandmother hired a new lawyer who actually knew what she was doing, and…” she trailed off, aware that she was sounding like exactly the kind of person Jess hated and, simultaneously, a little bit like Logan. 

“Yeah, I’m pretty sure being your mom’s fiancé got him exempt from your fancy lawyer’s gag order,” Jess said, breaking her gaze for a second and then returning it, full force. “How come you never told me about it?”

“About the boat?” Rory asked. Was this conversation really happening right now? Why had she decided to come to Luke’s in the first place? Clearly, she was never leaving her car again. “We haven’t exactly been in touch much the last few years,” she reminded him, trying to gain the upper hand in the conversation. There you go, Gilmore. Take charge, turn the tables on him, and distract him from the fact that if they weren’t standing in a dimly lit doorway it would be painfully obvious that she’d just been crying. “How’ve you been, anyways?”

“I don’t mean in the last few years,” Jess said. Dammit. Her tactic clearly wasn’t working. “I mean when I came and saw you at your grandmother’s house. Why didn’t you tell me that was why you dropped out of Yale?”

And there it was, possibly the only thing Rory liked talking about less than stealing a boat: her lost months. Sometimes she was able to go for a few days, or weeks even, without it springing to mind, but it always did, and with it the hot shame of knowing that she’d let Mitchum Huntzberger, of all people, derail the life she’d worked and fought and bled for, that she’d hit a deer for and begged for money from first her grandparents and then her father for, because she’d convinced herself he’d revealed what she’d always feared about herself: that she wasn’t good enough. And in light of what had just happened with Hugo Grey, Rory wondered for a second, just a single, secret second, whether Mitchum hadn’t been right all along. And just that second of profound self-doubt was enough to make her so angry at herself she felt like she couldn’t breathe.

“I don’t know what you’re talking about,” she snapped at Jess. What right did he have, to appear out of nowhere in a supposedly empty diner, to intrude on her alone time, and start talking about stealing boats and dropping out of Yale? “I don’t remember that.”

“Yes you do,” Jess said, frowning at her now, partly like he was confused that she was pretending she didn’t remember something that she clearly did (of course she did, him visiting was the only thing that had snapped her out of it, he’d practically brought her back to life with one conversation, by being the one who challenged her, he always challenged her, but she was at her limit and she just couldn’t take that right now) and partly angry that she was starting a fight with him out of nowhere. She couldn’t blame him, really, except, inexplicably, she did. “You know exactly what I mean. I came to see you, to show you my book, and we went out to dinner with your asshole boyfriend—heard you patched things up with him again after the engagement thing, congrats-“

“I love you,” she said. She’d had to say something, anything, to stop what he was saying, to derail where he was going, and for some reason she’d flashed back to the one conversation with him, years ago, that had shut her up completely at the time, when she was full of questions and demanding a confrontation and, in the shock and the aftermath of three words, he'd managed to completely slip out of it.

And apparently it worked on him too, because he stopped talking, shock written all over his face. And then he focused on her, and his expression changed, his eyes fixing on her even more intently, but she was too angry, too upset, to even try to figure out what was happening to him. Instead, she forged ahead, carelessly bringing down in flames the civil conversation he'd been attempting to have. "The infamous I love you. I remember THAT conversation with you. The one where you said I love you, and then you drove away? Remember that? That's a conversation that really sticks in my memory."

He opened his mouth to say something, to stop her, but Rory wasn't going to let that happen.

"And then remember when you called me at my high school graduation, and you didn't say anything, but I knew it was you, and I told you that I might have loved you too, and then you didn’t say anything back? That was a memorable one too. I’m so glad we’re here talking about all of these fantastic memories, Jess, I really am. But guess what? I’m the one who gets to leave this time. Have a good night.”

He looked at her like she’d slapped him. She turned around and ran back toward her car, the anger not nearly enough to chase away the shame and embarrassment that rolled over her like a wave.


	4. In Which Rory Circles Back

Rory yanked open the door of her Prius and slid back inside, not five minutes after she’d left it, somehow feeling even worse by a factor of about a million. She pulled out as fast as she could (yet still extremely safely, of course), and took off back the way she’d came. She should go back to Boston and hide in Lane’s apartment. Or to New York, visit Lucy and Olivia; they’d think it was spontaneous and quirky and not weird and desperate. Or to Hartford, to sneak into the bedroom that her grandmother still kept with its (expensively framed) NSYNC poster and its baby pink décor.

The bedroom in which she’d reunited with Jess, after she saw him skulking at the end of the driveway. After he’d appeared like something out of a book, exactly when she was least expecting him and somehow exactly when she needed him most. She remembered holding the book he’d written, sitting in her grandmother’s house where she was trapped in some kind of funhouse version of her life where nothing felt right, and thinking that somehow he still did. Feel right.

And now she’d just yelled at him, thrown the fact that he’d loved her once, back when she was a person who was actually capable of being loved, probably (She could practically hear Logan in her head again, telling her not to be so dramatic, Ace, doesn’t it seem like you’re blowing things out of proportion?). She hadn’t even seen him in years; this was probably the longest stretch of time she’d gone without seeing him, in fact. Luke kept her updated on him periodically; they’d be having a conversation about something else, and Luke would toss out the fact that Jess was doing well, that he was working on his second book, and then his third, or that his publishing house had expanded and was taking on new authors, and Rory would smile and say that was great, that she was glad he was doing so well, and to please tell him hello for her.

“I’ll tell him!” Luke always said, and she’d leave it at that, wondering, when Luke gave Jess his Rory updates, if he ever felt like she did, glad on the surface but with a sharp stabbing pain in her gut that never quite went away no matter how many years went by, a feeling that she refused to analyze or make anything more of than necessary. He was her ex-boyfriend. It was natural that it would feel strange hearing about him secondhand, when she wasn’t expecting it. That was all it was.

Jess had been back to Stars Hollow a few times, to visit Luke and Liz, but she always seemed to miss him. It wasn’t intentional—well, it wasn’t completely unintentional, but it wasn’t like she meant never to run into him again. She knew, intellectually, that she would, with Luke and Lorelai together for good this time, but she sort of felt like the longer she could delay that interaction, the better. Particularly because she brought Logan with her a lot of the time when she visited, and she didn’t have a great feeling about what would happen if she and Logan ran into Jess. Jess had only seen Logan at his worst, when he was drunk and jealous and chafing against his father’s restrictions, and Logan had an uncomfortable competitive streak when it came to her past relationships. The few times that Jess had come up in conversation, Logan had not-so-subtly belittled him, remarking on how little indie authors made, or how writing for a newspaper was so much more complex than writing a book. Rory hated when he was like that, so she’d just gradually stopped letting the topic arise altogether.

Logan really wasn’t what she wanted to be thinking about right now. Was it really just a few hours ago that she was standing in front of him? She couldn’t decide whether it felt like it was five minutes ago or at least a century and a half. He’d looked so normal when she’d come back to their apartment in Beacon Hill, straight from her conversation with Hugo. Sure, he’d been drinking, but that was hardly an indicator of anything.

“Ace, come on. What do you want me to say?”

She squeezed her eyes shut. No. Not going there. Not now, not again. She couldn’t do anything about that now; couldn’t even think about it, or she would start crying again. She wasn’t proud of it, but at least she could recognize it. No, the Logan situation was best left on the back burner for now.

She could do something about the Jess situation, though.

~~~

“Back for round two already?” Jess asked when she flung the door open, harder than she’d meant to since she hadn’t thought he’d leave it unlocked. He was still in the diner, sitting at one of the tables with a book open in front of him, his expression unreadable.

“I wanted to apologize,” Rory started, unable to help herself from attempting to sneak a peek at the cover.

Jess caught her look and flipped the book over. “The Nickel Boys. Colson Whitehead. You ever read him?”

“I picked up The Underground Railroad after it won the Pulitzer, it was devastating—“

“I don’t think you came here to talk about that, though,” Jess said, setting the book down and leaning back. “You want to apologize, go for it. I’d love to hear it.” He folded his arms and regarded her, and Rory almost lost her nerve, just from that look. He looked like he was disappointed somehow, or resigned, and she faltered. 

“I’m sorry. I was a jerk. I shouldn’t have said any of that. It was out of nowhere, and you didn’t deserve it, and I’m, well, sorry.”

He looked at her skeptically. “Is that it?”

“Did you want me to say something else?

He made an incredulous noise, somewhere between a laugh and a scoff, and ran his hand over his face. “Are you kidding?”

“No?”

“You walk in here—actually, no, you try to break in here like you’re in Ocean’s 8. I haven’t seen you in years, and I try to talk to you like a normal person, and you throw all that at me, and then you can’t even do me the decency of a real apology?”

“I did apologize,” said Rory. She could feel herself getting angry again, which was the exact opposite of what she was trying to do.

“You can’t just put all that out there and not deal with it, Rory. Is that really how you feel about me? That I’m just this terrible person you can just say anything you want to and I’m not going to feel anything?”

“No,” Rory said forcefully. “No, I don’t feel that way at all, I’m trying to tell you-“

“Because it’s not like you’ve been exactly perfect either. Or was it just more convenient to leave out that time you showed up in Philly and tried to use me to cheat on your boyfriend from your little recap?”

Rory squeezed her eyes shut. She’d thought she was done with the gut-wrenchingly shameful flashbacks for one night, but apparently not.

“How is Logan, by the way?” Jess asked, staring at her, and she was afraid he’d see right through her.

“Great,” she bit out. “He’s great. Everything’s great.”

“Good,” Jess shot back. “Good. I’m glad he’s great, although you’re clearly not.”

“What’s that supposed to mean?” Rory was pretty sure her eyes weren’t red anymore.

“Oh, I don’t know, you show up alone the week of your mom’s wedding, at midnight, looking upset, and instead of going to see her you try to break into Luke’s and you pick a fight with me instead. That might have clued me in on it.”

“I’m not having a bad night,” she lied. “Everything’s fine.”

“Fine? I thought it was great.”

“It is!”

They both took a breath, staring at each other.

“Okay,” said Jess. “Okay. What if we just…start over.”

“You want me to go outside and try to break in again?”

“No,” said Jess. “No. How about we just…Hey, Rory. Good to see you. You in town for the wedding?”

“Yep,” Rory replied, forcing a smile. “Yeah, I came early to help my mom get everything ready.”

“Me too. With Luke, I mean. Not your mom, obviously. I mean, I think it’s possible that she’s stopped drawing evil moustaches on all of the pictures of me, but-“

Rory hid a smile, a real one this time. And then she stopped herself. This wasn’t a good idea, this conversation. Being here with him, alone. At midnight. It was too familiar, and at the same time it felt like it had been way too long, and it was definitely too much. 

Unbidden, the thought of the way he’d looked when she’d seen him in Philly came to mind. Happy, finally. At ease, somewhere he belonged. Somewhere he seemed to want to share with her. The way he’d kissed her, as easily as breathing, and how her guilt had made her pull back. The look he gave her when he’d realized why she was really there.

“What if we had a truce?” she interrupted him.

“A truce? What, like we divide the town in half and you take the East side, I’ll take the West?”

“No, I’ll take the West side,” she said. “Andrew’s bookstore is on the West side.”

“Or you could just tell Taylor I’m here, take the whole town for yourself. He’ll have me chased out with torches and pitchforks within an hour.”

“You’re not giving him enough credit,” she said. “Ten minutes, tops. Less than that, if you remind him about the garden gnomes.”

“What will you do with the town, once it’s all yours?”

“I’m thinking I’ll start with the name. Rory’s Hollow has a nice ring to it.”

“It does,” he said, nodding. “Okay, a truce. A moratorium on talking about the past.”

“We don’t need to not talk about anything,” she said. “Just—we need this wedding to happen. They deserve it. And I take full blame for how tonight went. It’s my fault, I’m a terrible person, and I took it out on the first person I saw, and you didn’t deserve it. We can chalk this round up to you, okay?”

He nodded, looking at her like he saw more than she was letting on. “Sure, Rory,” he said. “I’ll see you around, then.”

She nodded, and had the door open when she heard his voice behind her.

“Rory.”

She stopped, and turned back. He was looking at her in that way he had, like he looked at her and actually saw her, Rory, not just whoever he wanted her to be.

“You look good,” he said. “And you’re not a terrible person.”

She didn’t know what to say, so she gave him a small smile and left the diner for the second time that night.


	5. In Which Rory is in Desperate Need of Coffee, But What Else is New

**Summary for the Chapter:**

> Rory has a rude awakening, is sent on a mission, and gets waylaid.

A loud and persistent knocking woke Rory up and, disoriented, for a moment she wondered if Paris had forgotten her key in a sleep-deprived haze from her overnight shift. Then she remembered driving from Luke’s to her mother’s house last night, betting on the late hour to help her avoid talking to anyone else after the Jess thing. She stretched her arms out and yawned, but the knocking refused to let her acclimate any more to the morning and so she reluctantly rolled off of the couch (she’d tiptoed to her old bedroom only to find every surface completely covered with wedding decorations and opted for the couch in lieu of potentially disrupting a system she was too exhausted to interpret but may, in retrospect, just have been an actual mess) and pulled open the door. 

“Grandma?”

Emily Gilmore fixed her with her signature patrician stare. “Of course it’s your grandmother, who else would it be?”

“Grandma, it’s-“ she glanced at her phone. “It’s 6:30!”

“So what?” her grandmother retorted. “Your mother is getting married in less than a week, young lady. You should have expected me days ago!”

“I only got here last night,” Rory yawned.

“Is that why you slept in so late?”

“It’s not—yes. Yes, that’s why. I got in late last night, and I haven’t really woken up yet.”

“Well, have some coffee,” said Emily. She frowned. “Where is your mother?”

“She’s probably sleeping,” Rory said. 

“Less than a week from her wedding?”

“Beauty sleep. It’s very important, I’ve heard.”

“Hm.” Emily turned her gaze to Rory and surveyed her critically, then hugged her suddenly. Surprised, Rory hugged her back. “I missed you, Rory. It’s good to see you in person rather than on the Facetime. I hate having to hold that phone up just to look at you.”

“I missed you too, Grandma,” Rory said honestly. Living in Boston made it nearly impossible to make a Friday night dinner with the commute, but she did visit Hartford when she was in Stars Hollow, and Emily had come to visit her in Boston as well (“Thank God you chose a city with proper restaurants and not just a McDonald’s”). She’d wanted to make sure she stayed in touch, particularly after her grandfather had passed away two years ago. Lorelai and Emily tended to butt heads if left alone together too long, and Rory often found herself in the role of long-distance referee, because it was just the three Gilmore girls now, without Richard, and Rory didn’t want anything to come between them.

“How have you been doing, Grandma? How’s the D.A.R.?”

Emily scoffed. “Tweeny Halpern and I have been trying to plan our latest fundraiser, and it seems that every caterer in Hartford has truly lost their minds. It’s absurd! I’m considering trying to tempt Sookie away from that inn of theirs.”

“Grandma, you can’t steal Sookie from the Dragonfly,” Rory said.

“I said I was considering it, not that I was doing it.” Emily raised an eyebrow at Rory. “You look tired. Why do you look so tired?”

“It’s 6:30, Grandma, remember?”

“Yes, but you’re young, and young people shouldn’t look so tired. Have you been getting enough sleep? Are you working too hard? Is everything okay at your online magazine?”

Rory had to stop herself from flinching at the barest mention of work, which wasn’t a good sign. Emily had a sharp eye for secrets, and if she sensed that Rory was hiding something, she wouldn’t leave her alone until she figured it out. At least her mom was safer—she’d give her space if she asked for it.

“Everything at work is fine, Grandma, I just got in late because I was talking to Paris and left Boston later than I meant to. Mom!” she suddenly called up the stairs, attempting to avoid further questions. “Are you awake?”

“…No,” came the groggy response from upstairs.

“Grandma’s here!” Rory called.

“It’s 6:30!” came the response. Then, “Am I dreaming? I had a dream once that you were downstairs telling me that Mom was here, and then I came downstairs and it was Elizabeth Warren. Elizabeth, is that you?”

“It most certainly is not!” Emily replied. 

“Mom, when I told you you could come over this morning to help work on wedding stuff, I was thinking you would come over more like 10,” Lorelai called.

“Ten o’clock is mid-morning, Lorelai, and if you wanted me to come over mid-morning you should have specified.”

“Rory!” Lorelai yelled. “I need coffee!”

Rory smiled weakly at Emily. “I’m going to go make some coffee.”

But when she got to the kitchen, she discovered one of the most terrifying sights possible in the Gilmore household: there was only enough coffee left for half a pot, at most. And with three Gilmores planning a wedding and needing sustenance, this just wasn’t going to fly.

“So, how’s Logan doing?” 

Rory jumped and nearly dropped the meager coffee provisions. Somehow Emily had sneaked up behind her during her coffee shortage trauma.

“You haven’t mentioned him yet. Is everything all right with you two?”

How did she do it? Rory wondered. Was there a certain Gilmore sixth sense you developed with time, or was it decades of experience in the social arena that allowed her to pick up on non-verbal cues?

“Logan’s good, he sends his love,” Rory said, shaking the bag of coffee and avoiding Emily’s eyes, trying to delay the inevitable.

“Rory, I just remembered, we’re low on coffee!” came the desperate shout from upstairs.

“I’ll go get some!” called Rory.

“And donuts!” said Lorelai.

“I’ll hit Weston’s!”

“Weston’s doesn’t have donuts! Go to Luke’s!”

“Luke’s is closed!”

“I know it’s closed, but Luke just remembered that he left the donuts there!” Lorelai cleared her throat. “Which I know because I am psychic, and definitely not because he is up here with me.”

“Lorelai, I’m aware that Luke is upstairs with you, as you have been living together for several years,” said Emily. “Rory will go and get the coffee and donuts, and I’ll start getting things organized down here.”

“Rory, take Grandma with you,” Lorelai said, a note of panic entering her voice.

“Nonsense. I don’t have time to be traipsing around all over town. Rory will take care of providing us with sustenance, and I will promise not to turn your house into the new headquarters of the D.A.R. while she’s gone. All right?”

“…okay,” said Lorelai.

“Be back soon!” said Rory, aware that if she wasn’t, things might escalate past a point that coffee and donuts could repair, and this wedding week was going to go perfectly, even if it killed her.

She rummaged through her haphazardly packed bag for something that wasn’t either pajamas or the sweater she’d worn yesterday. Normally Rory prided herself on her neat packing and overall preparedness, subscribing to the Gilmore philosophy of always bringing far more than you needed for any given event, but she’d been in such a rush to get out of the apartment last night that she’d been less than meticulous. She finally scored with another sweater, green this time, and black jeans, and headed to the bathroom to change and brush her teeth in record time, practically running out the door to keep Emily from intercepting her again and demanding more details about Logan, or possibly reading the entire debacle from her mind. She didn’t realize until she was actually out of the house that she’d just agreed to go back to Luke’s, where Jess was, not even six hours after she’d left.

~~~

The air was crisp, but in a good way, a way that woke her up enough to get the coffee that would fully wake her up, so Rory decided to walk to Luke’s. It would be fine, she thought. There was no way Jess would be awake before seven, right? Luke often woke up freakishly early, but that wasn’t necessarily genetic. Jess would be sleeping, and she could slip in, get the donuts, steal a bunch of Luke’s coffee so she wouldn’t have to go to Weston’s or Doose’s, and get out without him even knowing.

It was a great plan until she got to Luke’s and, through the window, could see Jess standing at the counter, eating a donut.

He saw her and waved, then picked up a napkin and started waving it like a white flag. Their truce. Well, at least she had accomplished that much last night. Rory sighed and went inside.

“Please tell me that’s not the last donut,” she said in greeting.

“You mean you’re not here cause you missed me?” Jess asked, mouth full of donut.

“No, I-“ Truce, she reminded herself. Be nice. What had he said last night? Talk to him, like a normal person, not like someone having an emotional breakdown, and definitely not like someone she thinks she can just be a jerk to and expect him to not feel anything. “My grandma showed up at my mom’s house at 6:30 and woke me up. Now I’m afraid if I don’t show up with coffee and donuts in the next ten minutes someone’ll get strangled by a veil. Do you really want that on your conscience?”

“I apologize, I had no idea the situation was that dire,” said Jess, reaching for another donut. At her panicked look, he laughed, pointing to a stack of pastry boxes on the counter. “Relax, there are like 40 donuts here. Do you really think I could eat all those?”

“Sorry, I must have confused you with me,” said Rory, relieved. “Thank God. The Gilmores are saved. Now show me to the coffee and no one gets hurt.”

“It’s back there.” Jess jerked his thumb at Luke’s back room.

Rory walked up to the counter and stopped, hesitating.

“What’s wrong?”

“I’ve never gone behind the counter before. Is this allowed?”

“Tell you what, I’ll give you permission. But just this once, Gilmore, understand? I catch you behind here again and I can’t promise Luke won’t ban you for life.”

To be honest, that wasn’t really what had Rory hesitating. It was that she’d have to pass right by Jess to get to the coffee, and now that it wasn’t dark and she wasn’t completely distracted by how puffy her eyes were and getting into unnecessary fights, she could see that Jess looked…really good. She didn’t think it was writing books that made your arms look like that, but something clearly had. He was wearing a tight T-shirt and jeans, and his hair was messy, like he’d just gotten out of bed too.

Which was NOT an image she needed to think about any further. Rory realized she was staring and hoped he hadn’t noticed, and, determined, headed around the counter, unable to avoid lightly brushing Jess’s arm as she walked past.

Those are not goosebumps, she told herself sternly as she located an industrial-sized canister of coffee in the storage room and grabbed it. It’s just cold. That’s all. 

When she re-emerged from the back, Jess had the pastry boxes stacked in his arms.

“Oh, great,” she said, reaching for them. “I’ll get going, then.”

He stepped back, the donuts just out of reach.

“Really? Give me the donuts, or I’m calling Taylor.”

“I’ll give you the donuts if you answer one question,” he retorted, a hint of a smirk at the edge of his mouth. “Why didn’t you tell me about the boat?”

“Jess!”

“You said you wanted donuts. Do you not want the donuts?” He made a sudden move, and then the donuts were hovering over the trashcan. “Cause I can just toss them…”

“No!” she yelped. No, she didn’t really think Jess would really do that to her—or the donuts—but she was having fun, for the first time since everything happened. And yes, he was asking the question she’d blown up at him for less than 24 hours ago, but he was teasing her, and he sounded happy, not accusatory, so…

“Fine,” she said. 

“Fine?” Jess smirked. 

“But not now.”

“You’re such a boat story tease.”

“We made a deal, right? This wedding is happening. And in order for the wedding to happen, my mom actually has to be alive to walk down the aisle, unless they quickly change the theme to The Walking Dead. And in order for that to happen, this coffee and these donuts need to make it back to her house, stat.”

“Stat, huh?” 

“Stat,” she confirmed. 

“Okay,” he said. He adjusted the stack of pastry boxes in his arms and walked toward the door.

“What are you doing?”

“I’m helping you carry the donuts. There’s no way you can carry all of these and the largest coffee can in existence.”

He had a point, but…”Um, you know my mother and grandmother are both there, right?”

“You may have mentioned that one or twenty times.”

She’d followed him outside of Luke’s by then, and they’d set off in the direction of her house.

“Okay, well, I’m just making sure you’re aware that I can’t be held liable if my grandmother kidnaps you and forces you to arrange centerpieces or embroider things or put together my mother’s dowry.”

“Your warning is appreciated, but unnecessary,” he replied. “I’m going to break Luke out.”

Rory hated that she felt slightly disappointed to hear that he wasn’t just walking over to help her. She shouldn’t be. She still had a boyfriend (if she ever forgave him), and it wasn’t like Jess was even thinking about her that way anymore. 

And she wasn’t thinking about him that way, either, for that matter. Not even a little bit. It was a road she’d been down before, and if last night was any indication, most likely better left alone.

“Going to do guy stuff?” she asked, aiming for lighthearted even though she was slightly disturbed by the direction her thoughts seemed to keep taking.

“I guess,” said Jess. “We’re going to go talk to the tent guy and pick up some of the furniture. But maybe we’ll shotgun a few beers while we do it, would that make it more manly?”

“It would, but it would not make it any less 6:30 in the morning.”

“I hate to break it to you, but it’s definitely not 6:30 anymore.” 

They’d arrived back at the Gilmore (now Gilmore/Danes) residence, and Rory was forced to admit that he was right—she’d taken way longer than she meant to. But it had been….fun, she supposed, so maybe it was okay if Emily and Lorelai had gotten into a minor altercation in the meantime.

“So,” said Jess. Rory looked at him. He was smiling slightly at her. “When am I getting the boat story?”

Her reply was cut off by Luke practically fell out of their front door, calling “Good to see you, Emily!” as he unmistakably attempted to flee the scene. He glared at Jess. “Where have you been?” he demanded.

Jess gestured to Rory.

“Rory!” exclaimed Luke. He hugged her, less awkwardly than he used to, and she hugged him back, grinning.

“Luke! Congratulations, almost!”

“Yeah, well, it was about time,” Luke said sheepishly. “Jess helped you with the donuts, then? Good. You better get those inside. Your grandmother has her party planner on speakerphone.”

“Oh, no,” Rory said. She awkwardly took the donut boxes from Jess, stacking the coffee on top, and peeked around it to look at him. “Thanks,” she said.

“You owe me,” he said. “Don’t forget. Later.”

“Later,” she confirmed. “Bye, Luke.”

“Bye, Rory.”

As they walked over to Luke’s truck, she heard him ask Jess, “So what’s later?”

“Nothing.”

Luke lowered his voice, but Rory could still pick out a few words as she pretended to fumble with the front door.

“…not really doing this again, are you?"

**Notes for the Chapter:**

> Longer chapter! More Rory/Jess! Emily Gilmore makes an appearance!   
> I hope you guys enjoyed this one; I'm having a lot of fun writing this. Much more to come :)


	6. In Which Rory Overanalyzes and Comes to a Conclusion

**Summary for the Chapter:**

> Rory tries to help Lorelai and Emily with wedding preparations, but she can't get Logan--or Jess--out of her head.

“…not really doing this again, are you?”

Luke’s words echoed in Rory’s mind over and over as she navigated the sometimes subtle, sometimes blatant efforts of her grandmother to alter the wedding that Lorelai had planned, and her mother’s subsequently gradually fraying nerves. As they assembled centerpieces, and Emily repeatedly asked why they couldn’t have hired someone to do this (“Because it’s fun!” “Is it, Lorelai? Is it fun? Is watching your mother work her fingers to the bone your idea of fun?” “I never asked you to come, Mom! You wanted to be included!” “Oh, so you don’t actually want me here, is that it?” “No, Mom, that’s not what I meant…”), Rory’s thoughts couldn’t stay on the centerpieces, or her arbitration efforts, or even the wedding itself. 

It hadn’t meant anything, had it? Luke could have been talking about anything Jess was doing, really. Going fishing, maybe, or being monosyllabic, or having nice hair. None of that really made sense, sure, but that didn’t necessarily mean that Luke was talking about her. And even if he was, it was probably just because he’d misinterpreted whatever he’d heard of their conversation. He probably thought that them meeting up later was some sort of plan on Jess’s part to get back together with her, even though of course it wasn’t. They hadn’t even talked in years, and she hadn’t exactly made the best impression last night. More like reminded him of her worst qualities, if she was telling the truth. He probably had hardly even thought about her until she almost fell into him last night; it wasn’t like he’d been secretly harboring feelings for her all these years. He had his own life, with his indie publishing house and his friends and his books.

Although the thought of him still having feelings for her had crossed her mind before, if she was being honest. Particularly after she’d read his second book.

Her phone buzzing on the table next to her interrupted her fruitless analysis, and the name on the display froze her in place. Logan.

She grabbed her phone before her grandmother could notice who was calling and comment on it, and tried to slow her breathing as she stared at the vases in front of her like they were a classic novel she was analyzing. She sent the call to voicemail without even thinking.

What had she thought, that he wouldn’t call her? That he wouldn’t try to reach out, after she’d left like that? Logan, who’d chased her to North Carolina to apologize, who’d had a coffee cart stalk her to get her back after their Ross and Rachel-esque “We were on a break!” pseudo-breakup? He’d given her the night, which maybe in his mind had been enough time and space, and had apparently decided it was time to talk now, after less than 24 hours. 

Rory didn’t want to talk.

Whenever they fought, Logan had a way of twisting everything in his favor. He’d argue around the situation, engaging with facts rather than emotions in a way that made her feel like maybe she didn’t know what she was feeling after all, like maybe he was right, in a way that felt like he was talking down to her even as he assured her he wasn’t. She remembered finding out that he’d cheated on her—with three of his sister’s bridesmaids, no less—and how he’d denied that it really meant anything, because he’d decided they were broken up even when she hadn’t, and he’d decided it was fine to sleep with whoever he wanted to even though she wasn’t, and it didn’t matter, anyways, because he loved her now, finally, and that should be enough for her.

She didn’t see how it could be enough this time. And she felt like she couldn’t breathe.

As calmly as possible, she set his number to Do Not Disturb, told her mother and grandmother she was going to the bathroom, and sat on the bathroom floor, staring at the missed call like something would change if she looked at it long enough, forcing herself to take deep inhales, hold them, and exhale through her mouth, like Paris did when she felt herself falling into a panic attack. No matter what she did, she couldn’t seem to completely block out what had happened last night.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Rory walked into Logan’s apartment (their apartment, he always insisted, even though Rory’s name was on a much less expensive lease with Paris across town), numb. She didn’t even remember how she got there. She must have gotten on the T, like she always did, and then walked the few blocks to Logan’s building, greeting the doorman politely, but she couldn’t remember it. She didn’t even feel like she was really there now, but outside her body, possibly still downtown in Hugo’s office, his words circling the room like vultures and tearing off pieces of her whenever they got close.

Logan was sitting on the couch, a glass of Scotch in hand and his laptop in front of him. He was probably working on something, an easier report he’d left for the end of the day, or prep for a meeting the next morning, and Rory realized in that moment that she had never cared about anything less than whatever the fuck Logan was trying to do after he’d ruined her entire life.

“Hey, Ace,” he called over his shoulder, not looking up. “Want a drink?”

Rory wanted to scream. Not even to scream at him, because words seemed to have deserted her while she was extracorporeal. Just to scream, and to feel like someone was hearing her. Instead, she said nothing, standing in the hall, not taking off her boots, not taking off her coat. Staring at the back of his head, and wondering how she'd gotten here so quickly (where had the time gone? The time she’d have normally used to think about what she wanted to say, to write it out even, in bullet points, to analyze, pro/con style?) when she wasn’t prepared to have this conversation.

But she didn’t scream. She forced her legs to move, to walk over in front of him, to cross her arms over her chest.

“I don’t want a drink. We need to talk.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

She couldn’t do this, she realized. She might be Rory fucking Gilmore, and she might be absolutely determined to help her mother have the wedding she’d always deserved, and not to hog the spotlight in the meantime by having an obvious emotional breakdown, but she couldn’t do this by herself. She had to talk to someone, and she had to do it soon, because if she had to keep all of this to herself any longer she’d explode. 

But she definitely couldn’t talk to her grandmother, who’d panic at the idea that Rory and Logan might not be destined to unite two prominent Connecticut families (no matter how much Emily hated the Huntzbergers, prestige trumped hate). And she was loathe to confide in Paris, whose main response would be “I told you so,” followed by a laundry list of everything she’d ever hated about Logan, starting with his hair and ending with his family. Lane would listen and would never judge her, but she wasn’t always great at giving advice—she tended to commiserate rather than give tough love.

That only left one option. An option Rory wouldn’t have even considered before she ran into him last night, or this morning, but Jess had already made her promise to tell him one story about her screwing up and derailing her entire life, so she’d probably be able to convince him to stay for a second one. 

She realized that she had no way to contact him until he got back from wherever he'd gone with Luke, and she walked into the kitchen, pacing, realizing that she wasn’t going to calm down until she had a solid plan in place for where and when she could vent.

And there it was, on the fridge, on a Post-It note in Luke’s handwriting, probably because he didn’t know how to program numbers into his phone: “Jess’s cell,” with a series of numbers beneath it. 

If that wasn’t a sign, Rory didn’t know what was. She pulled out her phone and texted him. 

“Hey. When’s later?”

She stared at her phone expectantly for a moment, then put it back in her pocket, only to have it buzz a moment later with a response.

“I’m assuming this is Rory?” the text read.

Rory scoffed and texted back. “Who else would it be?”

“Kirk, maybe? I haven’t heard from him since I got back to Stars Hollow, and I figured it was just a matter of time.”

“It’s Rory. When’s later?”

“I didn’t realize you were so anxious to see me again.”

“I’m not.”

“You texted me. How did you even get my number?”

“I asked Kirk.”

“You asked Kirk for my number because you just couldn’t wait until tonight to talk to me?”

“I got your number off the fridge. And you were the one who wanted to talk tonight, remember?”

“I remember.”

“So?”

“So what?”

“Jess!”

“Meet me at the lake at 10. You remember the spot?”

Rory was tempted to reply that she didn’t, but she did. Of course she did.

“OK. See you then.”

“Try not to miss me too much in the meantime.”

She stared, openmouthed, at her phone. Was he flirting with her? Text –flirting with her? After what Luke had said earlier, it almost seemed like he was hinting at something other than two old friends meeting up to honor a truce and tell a story, which was clearly all that was going on between them.

Clearly.

**Notes for the Chapter:**

> Thank you so, so much to everyone who's been reading and commenting. I really love getting to talk with people who love this show and these characters as much as I do, and it's really fun trying to give Rory the ending she deserves. 
> 
> Also, if any readers are in the U.S., please remember to register to vote! Vote early and/or vote by mail if possible; trust me, Rory would want you to. <3
> 
> Lots of Rory/Jess coming up in chapter 7. And maybe we'll finally find out some things? Who knows...


	7. In Which Rory Talks About the Boat, and Gets a Phone Call

**Summary for the Chapter:**

> Rory fulfills her end of the bargain by telling Jess the real story of why she dropped out of Yale.

Rory was glad they were meeting at the lake.

It wasn’t that she was ashamed to be seen with him, it was just that she knew how gossip spread in Stars Hollow and if one person saw her and Jess together, the whole town would know within an hour. Which wouldn’t matter, of course, since it was just talk, but it didn't really go along with the plan: this week was about Lorelai, and the wedding, and not about her, and she didn’t want the main topic of discussion at Lorelai and Luke’s reception to be whether her and Jess were secretly together when they unequivocally weren’t.

She pulled her peacoat snugly around her as she set off from the house. She’d told Lorelai that she was going to Miss Patty’s studio to get some work done, and that her new writing method involved very loud music and she didn’t want to keep her and Luke up, and that Miss Patty had told her she could use the dance space as a temporary office while she was in town. It was a pretty elaborate lie, and Rory would’ve felt more comfortable had it been closer to the truth, but she just couldn’t find a normal way to say “Hey, Mom, I’m going to hang out with Jess, who you’ve never liked, and who broke my heart when I was a teenager, and who I haven’t really spoken to in years, because of reasons I can’t tell you about.”

Her phone buzzed in her pocket, and she experienced a momentary panic thinking that it was Logan, even though she’d put him on Do Not Disturb. She checked it and answered, relieved and grateful to have a distraction from her thoughts even for the short walk over to the lake. 

“Hey, Paris.”

“Where are you?” came Paris’s demanding greeting.

“Oh, I’m doing great, Paris, and how are you?”

“I didn’t ask how you were since you’re obviously alive and well enough to answer the phone. What I don’t know is where you are.”

“I’m in Stars Hollow.”

“Why? I thought you weren’t leaving for another day. You and Huntzberger were supposed to spend a day doing annoying couple stuff before you went to the wedding. I remember because you mentioned the swan boats in the Public Garden and I almost threw up.”

“Plans changed, and I decided to head to the Hollow early.”

“Without Huntzberger?”

“He had to work.”

“But you were supposed to go together. Rory, what’s going on?”

“Nothing!” Dammit, she’d been doing so well, but she hadn’t expected a phone interrogation from Paris, who not only knew her too well to buy it but was always unhelpfully anticipating another screw-up from Logan.

“Where’s Lorelai? Put her on the phone, I’ll ask her.”

“I’m not home, Paris, I’m on a walk.”

“By yourself? At night?”

“No, I’m meeting Jess.” It slipped out before Rory could catch herself, but it wasn’t like it mattered, was it? It’s not like Paris would care who she was meeting.

“Jess, huh?” Paris’s tone changed, and Rory could swear she could detect a smile in her voice. “I guess that’s why Huntzberger couldn’t come early.”

“What? No! It’s nothing like that.”

“Sure it’s not. Way to go, Rory, you deserve to have some fun this week. I’m proud of you.”

Rory had clearly forgotten about the fact that, unlike most of Stars Hollow and, well, most of the people in her life (with the notable exception of Luke), Paris had never seemed to have anything against Jess. If anything, she seemed to take to him more than any of Rory’s other boyfriends or male friends in general, whom she typically despised. Rory thought it was probably because of the time they’d bonded while eating a truly absurd amount of takeout and discussing Jane Austen, and then Paris had covered for her after Dean showed up and the situation had looked…not great. Rory thought it was maybe because she and Paris had really bonded that night, as friends rather than frenemies or genuine enemies, and that Jess had become acceptable in Paris’s eyes through association, or maybe it was because he could actually keep up with hers and Rory’s intense literary discussions. Either way, when Jess came up in conversation, Paris was genuinely interested rather than snarky.

“Paris! It’s not like that, we’re just catching up!”

“Tell Paris hi for me,” a voice said in her other ear, and Rory jumped and dropped her phone, which luckily Jess caught before it fell off the edge of the dock.

“Is that Jess? Let me talk to him!” demanded Paris’s voice from the phone in Jess’s hand. Jess gestured to the phone, silently asking if it was okay. Rory nodded, still caught off guard by Jess appearing seemingly out of nowhere, although to be fair she hadn’t exactly been paying attention. Half a second later, she realized two things: she was already at the lake, and she definitely should not have let Jess talk to Paris.

“Hey, Paris,” Jess said into the phone. “Still in Philly, yeah. Working on my next one, but it’s slow going. And you’re living in Boston with Rory, right?”

Rory definitely hadn’t told him that, but maybe Luke had.

He laughed, and she leaned closer, trying to hear what Paris was saying to him, but she couldn’t quite catch it. “Oh, no, yeah, we’re just hanging out. Catching up, that kind of thing.”

Oh God. What had Paris just asked him?

Jess’s brow furrowed, and his smile turned serious. “Oh, yeah? OK, yeah, I got it. OK. I promise, OK? See you at the wedding, I assume.” He handed the phone back to Rory, an unreadable expression on his face.

“What did you say to him?” Rory hissed.

“Oh, nothing,” said Paris, who wasn’t even trying to lie well. “Have a fun night! Don’t do anything I wouldn’t do!” 

And she hung up.

Which left Rory standing on the dock, phone in her hand, staring at Jess, who had his hands stuffed into the pockets of his leather jacket and was looking out at the dark water.

“Thinking about going for a swim?” she asked, deciding the best tactic was to let Paris be Paris and pretend the conversation hadn’t happened until he let his guard down. Maybe she could get it out of him later.

“Nah, I figure if you get mad at me again you might push me in, so I’m figuring out the best escape routes.”

“I’m sorry,” she said. “Again, I mean. I’m still sorry.”

“It’s cool,” he said. “We’re good, remember? Truce?”

“Truce,” she agreed, and sat down on the dock, dangling her legs over the side. A memory hit her like a lightning bolt, of being seventeen and nervous, alone with Jess even though she should’ve been with Dean, using the Bid-A-Basket Festival as an excuse to finally talk to him, really talk to him, to figure out exactly what it was that drew her to him. Sure, he’d manipulated the situation to get her alone, but she didn’t have to agree to it, and she’d been surprised at how nice it had been, how easily they connected, how she didn’t have to censor herself or be afraid of boring him. 

Coming here was a terrible idea.

Jess sat down next to her, not touching her but closer than she’d have preferred.

“So, what did Paris want to say to you?” she asked, fake casual.

He chuckled softly. “Nothing.”

“Seriously.”

“Seriously, it was nothing. She hasn’t changed, huh?”

“Nope,” Rory said. “Paris will always be Paris. She’d doing her residency.”

“She said. Going to be a surgeon, huh?”

“Yeah.”

“So," said Jess. "Out of curiosity, it’s not like what?”

“What?”

“What you were saying to her when you said we were just catching up. It’s not like what?”

Rory could feel herself blushing, but it was dark enough that hopefully he couldn’t tell. “Oh, she was just making a joke.”

“Uh-huh.”

She needed to change the subject. “I needed to do something spontaneous.”

“That’s why you’re hanging out with me?”

“No, that’s why I stole the boat.”

He accepted the change in subject without missing a beat, and cut her a sideways look. “That really doesn’t sound like you. But then again, neither did dropping out of Yale.”

“Yeah.” She exhaled. “I was kind of going through something, and I thought that if I did something completely out of character to distract myself, I wouldn’t feel so terrible. And we were at the docks, so that’s where the boat came in.”

“We?”

“Me and Logan.”

“Huh.” It came out like an ‘of course,’ but Rory let it slide. “You were going through something. Before you dropped out of Yale?”

“Yeah.” Shit, Rory really hated talking about this. But she had to do it—they’d made a deal. (Of course you don’t have to if you really don’t want to, a little voice whispered in her mind. Just like with the basket. You wouldn’t be here with him if you didn’t want to be.) She needed to just say it, to get it over with.

“I had this internship, at a paper in Stamford. Logan’s dad got it for me; he was trying to apologize for something that had happened at dinner with Logan’s family, and he was trying to be nice. I thought.”

Jess’s jaw was tight, but he listened without comment, his eyes on her.

“It was really great, at first. I felt like I was really getting into the swing of things, the rhythm of the office. I liked everybody at the paper, and it felt like I was really doing something real, for the first time.” She smiled, but it wasn’t a happy smile. “Then he was leaving, and he wanted to give me some feedback, like a performance review. Except I don’t think that’s really what he was doing at all. I think he was just trying to…knock me down, see if I had the strength to get back up. See if I was good enough to be with his son. Or maybe he was just screwing with me, I don’t know.”

“What did he tell you?” Jess asked. It was too intense with him looking at her like that, so she looked away, out at the lake.

“He told me that I didn’t have ‘it,’” she said, with a wry smile. “That I wouldn’t make it as a journalist. He said he’d know, because he’d met so many people in the industry, and that I wasn’t going to be good enough.” Why was this so hard to get out, even now, this many years later? “That I didn’t have enough drive, or initiative, or whatever, and that I’d make a great assistant.”

Jess stared at her. “What a sexist dick.”

She laughed, surprised. 

“You believed him?” he asked. It was a fair question, even if it made her squirm.

“Yeah,” she said, looking down. “I respected him. He owns a ton of papers, he’s smart, and he’d been around me there for weeks. I was young. I felt like he knew what he was talking about, and I didn’t, and I felt like I’d failed.”

“You hadn’t even gotten the chance to start yet,” Jess said, softly. “How could you have failed?”

“It felt like I had,” she said. 

“Didn’t Lorelai talk to you, tell you he was wrong?”

“Yeah, she tried, but I didn’t listen. And by then I’d already stolen the boat, so there was that whole thing to deal with, too. It’s not her fault.”

“Of course not, it’s his fault,” said Jess. 

“So, then, after talking to him, I went to go find Logan, and he was at this party for his sister’s engagement, and the party was on a yacht, and I didn’t feel like hanging out with a bunch of rich people I didn’t know, and so I asked Logan if we could go out on another boat, and I knew he’d go along with it, and so…yeah.”

“What did he say about the newspaper thing? It was his dad that did that to you, right?”

“I didn’t tell him.”

“But didn’t he want to know why you wanted to steal the boat? He didn’t question the fact that Rory Gilmore, the most law-abiding person I have ever met, would suddenly get the urge to commit a felony?” 

“It wasn’t his fault,” said Rory, frustrated. “It was my fault. I let Mitchum get to me, and you’re right, I shouldn’t have.”

“That’s not what I said.”

“Yeah, it is,” Rory said. “Look, I’m not perfect all the time, okay? I messed up. I made a mistake. And then I made it way worse, and it just felt like going back to Yale made no sense if I couldn’t be a journalist anymore, and I wanted to take some time and just think about it, but then I got into a fight with my mom about it and everything kind of snowballed and I had to move in with my grandparents, and then I had to do 300 hours of community service so I had to get a job, and the only job with flexible enough hours was with the D.A.R., and…” She sighed, putting her head in her hands for just a second. It was almost over. “And then that’s when you showed up.”

“Rory. Hey.” 

She didn’t look up. God, this story made her sound horrible. Insecure, and broken, and privileged, and horrible.

“I messed it all up,” she said, and in spite of all the years that had passed, in spite of everything, she could feel tears starting to form in her eyes, so she kept them hidden. “I’m sorry, I shouldn’t have told you all of this. I’m pathetic.” She gave a sad little laugh.

“Rory.”

She felt his arm go around her shoulders, and she really wanted to cry now. She shouldn’t be doing this. She shouldn’t be here, in this place, with him, especially not now. But he was warm, and he was there, and she leaned into him, letting him pull her to his side. She sniffled a little, wiping her face and finally bringing her hands down to her lap. She looked up at him, afraid of seeing judgment there, of seeing the worst things she thought about herself reflected on his face. But he was looking at her like he always did. Like he saw her. Not just the good parts, but not just the bad parts either.

“You’re not pathetic,” he said. “That was messed up. What that guy said to you? Said to a college student interning for him? That was beyond inappropriate, but it was also dead wrong. You know it, and I know it, and everyone who actually knows you knows it. You’re the smartest person I know.”

“No, I’m not,” she said.

“Yeah, you are. And I just got off the phone with Paris, so that’s saying something.”

“I’m not smarter than Paris.”

“You beat her for valedictorian, didn’t you?”

“You remember that?”

“Of course I do,” he sighed. “Rory, nobody expects you to be perfect. And this is coming from a guy who’s never even come close.”

This is perfect, she thinks, us, right here, on this dock, with Jess somehow not hating her or looking down on her even though she’d just exposed one of her worst sides to him. And then the guilt hits her, because she hasn’t told him the worst thing yet, and maybe that would make him change his mind. She presses into him and leans her head on his shoulder, bracing herself for what she’s about to do next.

“Jess?” she asks.

“Yeah?” His voice is rough, and one of his hands reaches over and threads through hers. She shivers, and it’s almost enough to make her stop talking, but she can’t. She can’t be that girl that doesn’t face the worst parts of herself, even if the idea of telling this guy about what happened makes her want to shrink back into that humiliated college student she once was and to let other people take care of her problems while she just tries to escape into it all. 

But she’s not that girl anymore. She’s grown up, she’s gotten stronger, and she just needs this, just needs to get this over with so that she can be an adult and get through her mother’s wedding with minimal emotional upheaval. 

But she also really, really doesn’t want to move away.

So she decides, as a compromise, that she won’t. She thinks distantly that Paris, at least, would approve.

“Jess?” she says again.

“Yeah?” he repeats, grinning a little this time, and moving closer to her. 

She needs to shut that down, quickly.

“Thank you, so much, for listening to all that, and I’m sorry that I basically just forced you to sit through me venting to you about my college drama for an hour.”

“Um,” he says, clearly caught off guard a little by the change in the atmosphere. “I asked you to tell me. You didn’t force me to sit down and listen to you. I wanted to.”

“I know,” she says. “And I don’t want to take advantage of your admittedly stellar listening skills, but I was wondering…if I could tell you about one more time that I royally screwed up.”

He squeezed her fingers, and she could feel her heartbeat speed up. This is fine, she told herself. We’re just old friends, hanging out. This doesn’t mean anything. We’re just talking. And sort of cuddling. But in a friend way. “Does this have anything to do with you yelling at me last night?”

“Yes,” she says, mentally pulling herself back together. “If you don't mind listening to me for a little while longer, I’d like to tell you what happened yesterday."

**Notes for the Chapter:**

> I'm evil, I know! Chapter 8 will be up sometime this week ;)   
> Thank you all for reading!!!


	8. In Which Rory Does a Flashback

**Summary for the Chapter:**

> Rory tells Jess what happened.

**Notes for the Chapter:**

> I'm so sorry this took me awhile to update! I wanted to get it right, and I've been working on this chapter and future chapters simultaneously, so it took me a little bit longer. Hope you enjoy!

“If you don’t mind listening to me for a little while longer, I’d like to tell you what happened yesterday.”

Her words lingered in the crisp night air as he looked at her. His expression was more serious than it’d been a moment ago, when Rory thought he might have been—she didn’t know what he’d been doing, and she really shouldn’t speculate.

“Yeah,” he said, his voice rough. “I mean, I don’t mind.”

“It’s bad,” she said, her voice cracking slightly. “I—I messed up. And I can’t talk to my mom about it, because of the wedding, and I just—I don’t know what to do.”

“It’s okay,” Jess said. “Rory, I could tell something was going on with you, and you can tell me. You can tell me anything.”

“Why,” she hesitated, and then kept going. “Why are you being so nice to me?”

He was quiet for a moment. “You know why,” he finally said.

Rory thinks about saying that she doesn’t, but that would sound like she was asking for an explanation, which she definitely does not want to do. You don’t want to go down that road, she tells herself. Not again, and definitely not now.

He lets the moment pass, instead saying, “Lay it on me, Gilmore. What the hell happened yesterday?”

Rory takes a deep breath and tells him.

~~~

It had been a typical Friday at the office, until it hadn’t. 

Rory had been spending the day enmeshed in research about an article highlighting a new tech startup working on developing on a more secure form of password storage that could link all of your separate accounts with precautions against data breaches; it sounded like something that would be undeniably useful, if it worked and didn’t get hacked itself, and she was trying to learn enough about the project to take a stance in her article. It meant learning a lot of technical jargon she was unfamiliar with, but that was one of the things Rory loved most about being a reporter—it was an excuse to nerd out about different topics on a regular basis, doing deep dives into areas of research she never would have even considered looking into. And then, mid-afternoon, she got an email from Hugo asking her to come see him at the end of the day.

She’d been mildly nervous, but hadn’t panicked; her initial thought was that he hadn’t been impressed with her last piece discussing threats to the Affordable Care Act, which she’d co-written with another reporter and hadn’t had full control over. She worked on her defense in her mind: she didn’t want to blame the other reporter, who’d worked with Hugo for longer than she had, but she didn’t want to take the brunt of the critique if it wasn’t deserved, either. She was trying to find the right diplomatic wording as she knocked on Hugo’s door, opening it without waiting for a “Come in,” as she knew he was usually so engrossed in what he was reading he didn’t hear her.

But Hugo wasn’t reading when she came into his office. He was sitting back in his chair, staring at the wall, arms folded in front of him. Like he was deep in thought, or like he’d been waiting for her.

“You wanted to see me?” Rory asked. She hated the higher pitch her tone still took on when she spoke to her boss; she wasn’t really nervous around him, but it was always ingrained in her to make a good impression on the people around her, and scrupulous Gilmore politeness sometimes sounded a bit more girlish than she’d like.

“Yeah,” he said, clearing his throat. “It’s about your article.”

“Look, I know the tone of the piece was a bit pessimistic, but I really think that—“

“Your other piece,” Hugo said. “State Senator Howard.”

It wasn’t just a piece, to be fair. It was a series Rory had worked on almost exclusively for a few months straight, which had ended up being some of the most difficult months of her career. After a tip had gotten her started, she’d gradually uncovered that George Howard, a state senator in Connecticut, had been taking bribes from several prominent business owners in exchange for voting their way on certain legislation that came across his desk. As political scandals went, it was a relatively minor one given its small scope, but Rory had been truly proud of it—not just because of the hard work she’d done, but because she’d accomplished something, revealed something, gotten justice, in some small way. The case would be tied up in court for awhile and there was still a strong chance that Howard wouldn’t actually be convicted as a result of the scandal, but he’d been forced to resign because of it, and that, however small, was something.

“What about it? Did you want me to do a follow-up?” she asked. There hadn’t been anything new for awhile, but maybe he wanted a piece on the fallout, or—

“No,” he said forcefully, and Rory was surprised. Hugo was the definition of a mild-mannered guy, unless he was ranting about the president.

He took a deep breath. “No, Rory, I definitely do not want you doing another follow-up. Want to know why?”

“Yes,” she said, frowning.

“Because your future brother-in-law Josh Levin just announced he’s forming an exploratory committee to run for George Howard’s seat.”

Rory felt her stomach drop, and she felt for a moment like that couldn’t possibly be what he’d said. Honor Huntzberger’s husband, running for state senate? It couldn’t possibly be true. Josh was a lawyer, and although they frequently talked politics when she and Logan met them for dinner, neither of them had ever alluded to him running for office.

“Interesting timing, too, with that Antitrust bill being put on the table for the next session.”

Antitrust bill? Rory’s confusion must have shown on her face, and Hugo smiled, but not happily. “I don’t exactly know the logistics of it yet, but if a few more votes swing the way your future father-in-law likely wants, he’ll be able to buy the Chronicle if it gets shot down.”

No. No, this couldn’t be happening. There was no way this was happening. And if it was, maybe it was just a terrible coincidence. Maybe Josh had just suddenly decided he was ready to run for office, and when a vacancy appeared that needed a special election, he decided he might as well give it a chance. And maybe Mitchum just happened to have been stonewalled by antitrust legislation as he was trying to purchase his next newspaper, which he’d been touting as a huge get for his corporation, and the legislation just happened to be something that Josh could have some say in, if he was elected. Sure. All of that was possible.

Except that it wasn’t.

Hugo laughed drily. “If I’d thought for a second you knew about any of this already, the expression on your face just told me otherwise. You don’t exactly have a great poker face, Gilmore.”

But Logan does, she thought. Because he’d looked completely normal as he’d introduced her to Howard’s aide at a party. The aide who had become her primary source for exposing Howard’s corruption. The aide who just happened to be a friend of Logan’s, and who Logan assured her would be able to entertain her while he had to go take a call.

“Hugo,” she said, the word sticking in her throat. “I swear. I didn’t know.”

“I know,” he said. He took a swig of coffee from the ever-present mug on his desk. He could have been a Gilmore with all the coffee he drank, Rory had told him once, standing right where she was standing now. How the hell had it come to this? “But it looks bad.”

“I don’t—understand,” said Rory, who was still trying to reconcile this family, the ones who could do this, with the family she knew. Honor, who took her shopping and told her funny stories about her and Logan growing up. Josh, who was shyer than Honor, but who loved her enough to brave the expected wrath of her parents and marry her. 

And Logan.

“Like I said, I don’t have all the details yet,” Hugo said. “I’m still putting the pieces together. Figuring out exactly how much trouble we’re in here.”

“I can help,” Rory said quickly. “I’ll help you. We’ll figure it out. I’ll make it right, I promise.”

But he was already shaking his head. “Gilmore, I need you off this story. It’s bad enough as it is, I don’t want anybody to get wind of you asking questions. You know what the implications are here. You’re smart.”

“That seems debatable right now,” Rory muttered. 

“You were planning on taking a few days off next week anyways, for your mom’s wedding, right? Take the time. Head down a few days early.”

“But I need to fix this,” Rory said. She sounded weak and small, even to her own ears. “Please, let me fix this.”

“You can’t,” Hugo said flatly. “You can’t. Gilmore, I like you, you’re a great reporter, but this is really bad, and I need you out of this office while I figure out the extent of it. Okay?”

Everything in her rebelled against leaving his office, against leaving the paper, against fighting back, researching, fixing. But she knew he was right, and that was the only thing that made her nod and tell him again how sorry she was, that she didn’t know, to have a good night.

There was one thing she could do tonight, though. She could talk to Logan. Sure, she could also head to Stars Hollow and postpone the confrontation, but what good would that do, really? She was already screwed.

She already had her answers, technically. But she needed to hear it from him. 

~~~

“I told you it was bad,” she said with a weak smile. Jess hadn’t said anything yet, but he’d kept his arm around her the entire time, which meant he couldn’t hate her that much. 

Or maybe he was just being polite. Although that wasn’t really Jess’s style. He didn’t do things just to be polite.

“I’m an idiot,” she continued. “I had no idea. None. They never said anything, and nothing in my research showed anything remotely connected to the Huntzbergers. I didn’t even suspect anything when Logan introduced me to that guy at the party; I thought it was really just some friend of his in politics who would have something more interesting to talk about than wine or furniture or real estate, which is what most people are talking about at those parties.” She shook her head. “I’m so humiliated. I thought I was a reporter. A real reporter. I’d thought I’d done something good, when all I did was play right into their hands, and do exactly what they wanted me to do. I’m so stupid.”

She wasn’t going to cry again. She was tired, and she’d cried enough last night to last her awhile. But she wasn’t yet out of steam on verbally berating herself, it seemed. 

“My career’s over,” she continued. “It has to be. People are going to figure it out, that I’m with Logan and Josh is his brother-in-law. And maybe even put the pieces together about the business deal, too, and what that’s doing for the family. Hugo’s going to fire me when I go back next week. He’s going to have to. It’s an ethics issue. He can’t have a reporter who’s ethically compromised. And no one’s going to hire me after this all comes out.”

She stopped talking abruptly, because Jess was holding her hand again. He stroked his fingers down hers lightly, and she shivered. He gave a small smile, staring down at their entwined fingers, and then he leaned forward and kissed her.


	9. In Which Rory Doesn't Know What Just Happened

Jess leaned forward and kissed her, and Rory froze. His lips brushed hers gently, softly, and she was surprised, because in the heat of the moment that wasn’t what she’d been expecting. Not that she’d been expecting this, or wanting this, of course.

Without thinking about it, she felt herself leaning into him, letting him kiss her, while her hand reached up on its own volition to brush his hair back from his face.

And then he pulled back, smiling at her slightly, his fingers tracing her cheek.

“I’m sorry,” he said. “You didn't finish your story.”

At that moment, Rory had no memory of telling a story, and was sure that whatever it was couldn’t have been important enough for him to stop, until a fraction of a second later it all came crashing back. Hugo. George Howard. Mitchum Huntzberger.

Logan.

She squeezed her eyes shut, trying to block it all out, trying to go back to seconds before when, just for an instant, everything had felt right. It wasn’t easy; her brain kept breaking in with thoughts like “what about Logan” and “wasn’t I just talking about what a terrible person I am,” but she forced herself back to the present, back to what was happening now, which wasn’t what she’d meant to have happen when she came to the lake tonight but was somehow exactly what she hadn't realized she'd wanted, and which was now the only thing keeping her other thoughts at bay.

“You can keep going, if you want,” Jess was saying. “But I’ve got to be honest, I’ve been wanting to do that ever since you tried to break into Luke’s.”

Honestly, that was what did it. She didn't want to think about anything else, or care about anything else, not when he was saying those things to her and looking at her like that.

She leaned in and grabbed the collar of his jacket, kissing him roughly, disrupting both her train of thought and his attempt to bring them back to what was happening before, which was safe and friend-like and, well, not this.

He kissed her back just as roughly, meeting her with what she needed, stroking his tongue into her mouth and moving his hand to her waist as he drew her in. Distantly, she remembered the last time she’d kissed him, at his publishing house in Philly, and it comes crashing back to her exactly how wrong it was for her to be doing this now, especially when he’d brought that up with her just last night.

Because, yet again, he thought she’d broken up with Logan.

And, yet again, she hadn’t. 

She was stuck in some kind of screwed-up pattern with Jess, and with Logan and Jess, specifically, and she didn't know why this kept happening, but part of her knew that it had to be her fault.

She pulled back again, gently this time, and Jess reached up to brush his thumb across her lips.

“We should—talk,” she said, somehow a little out of breath.

“You’re right,” he agreed. He was grinning at her, looking more relaxed than she’d seen him this entire visit, as he stroked his hand through her hair. She shivered. “I didn’t tell you what I thought about your story.”

“No, that’s not what—I mean, it’s not what I—“

“It’s okay,” he said. “I get it. What they did to you, that’s absolutely fucking horrible. I didn’t mean to ignore you, or undermine what you were saying. But, Rory,” now he was twining a strand of her hair around in his fingers, and she was somehow absolutely, completely, incomprehensibly into it, “You’re going to get through this. I know you are, because I know you. You’re smart, and you’re strong, and you can get through this. I’m so glad you’re out of there, and done with that guy and his fucked-up rich family. You’re so much better than that.”

Oh, God. What the hell was she doing? He was never going to forgive her for this. She shouldn’t be letting him keep talking, letting him be sweet to her when she absolutely, definitely didn’t deserve it.

“Jess,” she said. 

He looked at her, and she could tell the instant he saw it in her eyes. He didn’t pull his hand away from her hair, but she could see his expression shifting, becoming closed, difficult to read.

“Rory,” he said. “Please don’t tell me what you’re about to tell me.”

“I didn’t mean—I didn’t know you were going to do that. I shouldn’t have—I mean, I left, I told him I needed space, time to think, but I didn’t actually end it. I mean, officially.”

“You didn't end it," he said, like maybe that wasn't the worst thing in the world. "But are you going to?"

She couldn’t read his expression. She hated that sometimes she had no idea what he was thinking. And she shouldn’t hate it; she shouldn’t feel anything about it at all, and she didn't, she didn't really, or maybe she wouldn't if this night hadn't gone like this.

“I—“ she hesitated, and he nodded, and let go of her.

“Jess, wait,” she said. “I mean, it’s not really something I can forgive, but it just happened all the sudden, and I need time, I need to process it, I don’t even know all the details, I don’t know how much he was really involved—“

“But you know he was involved, even if you don’t know how much,” he pointed out. He was zipping up his jacket, and Rory really, really didn’t want him to leave, and she wasn’t even sure why, since she shouldn’t be here, doing this with him, in the first place.

“If you had let me finish—“

“I’m sorry,” he said, “That I kissed you, if that wasn’t what you wanted, but you kissed me back, Rory. Are you going to pretend you didn’t?”

Rory didn’t respond. She was completely at a loss right now. She’d just spilled her guts and kissed her high school boyfriend the day after the worst day of her life, and she had nothing left to say.

Clearly interpreting her silence in a negative light, he nodded at her, like he was confirming something to myself.

“Have a good night, Rory.”

“Jess-“

“What? Do you have something you want to say to me?” He looked back at her, searching. “Or do you just want someone to talk to about your boyfriend?”

He’d been beyond understanding with her tonight, but those last words hurt. Because she deserved it, and because he wasn’t wrong.

“I’m sorry,” she said. It felt like that was all she’d been saying to him since she got back to town. 

He shook his head, and walked away. Rory was left standing on the dock, her arms wrapped around herself, because it suddenly felt a lot colder without Jess next to her. She tried not to think about what had just happened, and found herself thinking about the only worse thing she could instead.

~~~

Half an hour after her disastrous meeting with Hugo, she’d stood in front of Logan, just staring at him. She wasn’t sure what she was going to say until she said it.

“I talked to Hugo today.” Her voice sounded deadened, flat. She didn’t even feel like she was hearing herself, that maybe she’d only thought it, until he responded. 

“Sounds like it didn’t go well? Have a drink and tell me about it.”

“It might,” she said, “Go faster if you would tell me about it.”

He was smiling at her, that wide smile he had where his eyes crinkled, and if she hadn’t known better she’d have sworn he had no idea what she was talking about. Just like she’d had no idea about the other girls he’d slept with until they literally said it in front of her.

But she knew better, this time.

“I’ve never thought you were stupid,” she says now. “So why don’t you stop pretending you are, and have the balls to tell me to my face what you did to me.” She was surprised at herself after the words left her mouth, but she didn’t let her expression waver. This was torturing her, and she needed him to be saying something back, to be feeling something. To torture him back, even just a little bit.

“Ace, what are you talking about?”

She waits a beat, giving him one more chance to dig himself just a little bit out of the hole he’s in, but he doesn’t budge, expression still as innocent as when she walked in. 

“Josh,” she spits out at him. “Josh is running for Howard’s seat. The seat is that’s vacant because of the source you referred me to. And it’s your father’s company, your family’s company, that’s going to benefit from the whole thing. And it’s me who’s going to look like a biased, ethically compromised reporter who’s only trying to further her boyfriend’s business interests. And you knew—“

“Wait a second,” Logan said. “Hold on just a second. Are you seriously accusing me of setting all this up?”

“Are you seriously telling me that you didn’t?”

“Ace, this was not me. Does this sound like me? This has my father written all over it.”

“Mitchum didn’t tell me to talk to Howard’s aide, Logan. You did.”

He rubbed a hand over his face exasperatedly. “I only told you to talk to that guy because he was a nice guy! I thought you guys would be able to talk politics! I thought I was saving you!”

She stared at him, trying to figure out if there was any chance, any chance at all, that he was telling the truth. It sounded reasonable, believable even, to have the whole thing be Mitchum’s fault. To have Mitchum, yet again, playing the villain in her life. But she knew things like this didn’t happen in a vacuum, and some coincidences were too perfect to be believable.

And, deep down, she knew she couldn’t trust him right now.

“We said we weren’t going to lie to each other,” she said steadily, looking him right in the eyes. 

He sighed and looked away first. “Look, my dad told me that the aide might have some dirt on Howard. I thought it might be good for you to cultivate a political source. So that’s why I introduced you. But I didn’t know that he was thinking about putting Josh up for Howard’s seat, I swear.”

She nodded. “Did you assume it would be another one of his cronies, then? Because I’m sure you know about the antitrust stuff. It’s your company too, after all.”

“First of all, it’s not my company, not until my dad retires, and maybe even not then, if he ever does what he’s threatening me with constantly and cuts me off. And second of all, no. I had no idea about the rest of it. Rory, I swear to you.”

She takes a second to digest this, and he presses forward, sensing an advantage.

“It sounds bad, Rory, I get that. But it’s honestly not as bad as you’re thinking. No one’s going to connect you to this—we’re not married, we don’t live together, you don’t take any money from my dad’s company. You’re clean. And the site you work for isn’t exactly the New York Times. It’s a small-time story, state politics. No one’s going to look at it too closely; the Howard thing hasn’t been on anyone’s radar for months.”

She closed her eyes, unable to believe what she was hearing.

“So, first you tell me you don’t know what I’m talking about. Then you do know what I’m talking about, but you weren’t involved. Then you were involved, but only a little bit, and then you decide that it doesn’t even matter either way, and neither does my career, apparently.” She shook her head in disbelief. “I can’t believe you right now, Logan. I honestly can’t even believe that this is happening.”

“So don’t believe it! Trust what I’m telling you!”

“Maybe if you had your story straight, I would have,” she shot back. “But right now, I can’t believe a single thing coming out of your mouth.”

“Are you kidding me? After everything we’ve been through, you don’t trust me?”

She took a deep breath. “Not right now, I don’t.”

He looked at her, pleadingly. “So where does that leave us?”

She didn’t know what to tell him other than the truth. “I need space. I need time. I need to think about this, and I can’t do it with you.”

“Are you breaking up with me?” he asked. There was a slight teasing hint to his voice, like he was trying to lightheartedly take them back to one of their old arguments, one where they’d finally agreed on a policy that any future breaks vs. break-ups had to be explicitly stated in a way that left absolutely no room for misinterpretation by either party. It wasn’t cute right now.

“No,” she said. “I don’t want to make any decisions right now. I’m too upset, and I need to think, so I’m going to go.” She nodded, one decision, at least, made for now, and headed for the door.

“Take all the time you need,” he called after her. “I’ll still be here. Rory, I love you. Please don’t let this be what comes between us.”

She didn’t respond, but didn’t slam the door behind her, either. She just left for hers and Paris’s apartment, packed as quickly as she possibly could, and got in the car.

**Notes for the Chapter:**

> First of all, thank you so much for all the feedback about the last chapter; I really appreciate it, since it was probably the one I've been most nervous about posting. Hopefully this chapter doesn't make you hate me too much. ;)


	10. In Which Rory Makes a Pro/Con List

Stumbling into bed late for the second night in a row, combined with a complete emotional upheaval, did not, it turned out, have a great effect on Rory’s energy levels. She’d meant to sleep in, but she found herself slipping in and out of stress dreams involving a dizzying combination of snobby Chilton students mocking her for not understanding how business and politics worked in their upper-class world; herds of deer trampling her Prius while she drove frantically from Boston to Stars Hollow; Paris announcing that she was dating her grandfather, who, it turned out, had faked his own death in order to carry out the relationship in secret; and Dean, who in her dream was nine feet tall, accusing her of cheating on him with Jess, and who, as she was about to answer him, turned into Logan. She’d lost count of the number of times she’d awoken during the night, and around 6:30 a.m. (Emily Gilmore would be proud) she gave up and went to make coffee.

Her eyes felt dry and sticky, and her hand was almost shaking as she reached for the coffeepot. She felt like she was controlling her body like a robot, like she was telling herself to pour the coffee and drink it, but that she was watching herself rather than really doing it. She knew she wasn’t making sense, and she sat down at the kitchen table endeavoring to drink her coffee as quickly as she could without actually scalding her tongue. She’d feel better after some coffee, right? She always did.

When she looked up and saw Jess’s cell number still stuck to the fridge, though, she was forced to admit to herself that coffee might not be much help this time. So, to torture herself further, she checked her phone to see exactly how many calls and texts from Logan she’d missed yesterday.

Several, it turned out. All of which consisted of apologies and begging her to talk to him, after a courtesy “I know you asked for space, but…” tacked on at the beginning. How could he not understand that this wasn’t what she needed right now? She’d made it clear to him that she had to think, and honestly, she’d barely had time to do that. She wasn’t ready. She deleted his messages methodically and set him back to Do Not Disturb, then took another gulp of her coffee.

Jess hadn’t called or texted, of course.

She didn’t know why she was even thinking that. Jess was actually a good person, it turned out, unlike her, and she’d clearly messed things up with him one too many times. Probably he was now counting his blessings that he only had to deal with her for this one week, and then they could go back to never interacting and dividing up Stars Hollow holidays with Luke and Lorelai on an alternating basis.

Okay. She really, really needed to stop thinking about Jess, and start thinking about Logan.

Logan, who was in Boston, and who therefore had no idea that she’d kissed Jess last night.

Logan, who she’d also never told about going to see Jess in Philadelphia after she’d found out he’d cheated on her.

It’s not the same, she told herself. You kissed someone else; Logan slept with three of his sister’s bridesmaids and potentially destroyed your career, then denied it. It’s not the same. Don’t you dare blame yourself for what he did.

Jess had asked her, last night, whether she was planning on breaking up with Logan. Worse, he’d assumed that she already had.

She hadn’t wanted to get into it with him, but it wasn’t that easy for her. She wished that it was, in a way. She wished that she could so easily stand up for herself the way that Jess seemed to think she was capable of doing, and just end it, and not let doubts creep in every time Logan opened his mouth.  
But it wasn’t that simple. When she thought about her relationship with Logan, it wasn’t just one night she had to take into account, no matter how devastating that night was. It was years of them being together, of growing together, of supporting each other. It was living together and then breaking up and then rekindling things when it seemed like him moving back to the East Coast meant they were meant to be, somehow. It was them promising they’d be better for each other, that they’d communicate more, that they’d support each other rather than making about all about just one of them.  
It was Logan proposing to her at the graduation party her grandparents threw for her, and it was that he’d been so sure that she would say yes when it had never even crossed her mind that he’d ask her so soon. It was the look in his eyes when she’d told him no, and he’d told her that he didn’t want to be with her if that was her answer.

So no, she couldn’t automatically break up with him. She wasn’t the face-slapping, drink-tossing, door-slamming type, even after what had happened. She was Rory Gilmore. She was a planner, and a list-maker, and when she was overtaken by emotion she turned back to logic every time, or at least she tried her best to. 

It was strange, she thought, that the only times she didn’t first turn to logic seemed to happen when she was around Jess.

Shaking the thought from her mind, since she was focusing on the Logan situation at the moment (one emotional crisis at a time, she told herself, there’ll be plenty of time to beat yourself up about the Jess situation later) she went back to her old bedroom and grabbed one of the ubiquitous journals that lay scattered on her shelves. It was time for a pro/con list. 

Pro/Con List: Logan Huntzberger

Pros:

-We’ve been together for years

-Loves me

-Smart

-Spontaneous

-We have a life together in Boston

-My grandmother loves him

Cons:

-Evil father

-Possibly evil sister/brother-in-law

-Evil (but less scary) mother

-If we get married, they will become my evil in-laws, forever

-Basically, that wedding would be like the part in the horror movie where everyone is screaming at the female lead to GET OUT NOW, SAVE YOURSELF (Not that I want to get married?)

-Cheated on me (caveat: that was years ago, and he genuinely does not think he cheated)

-My mother has never really liked him

-Involved, in some degree, in Howard situation

-Lied to me about his involvement

-I still don’t know exactly what he knew or when he knew it

-I don’t think I can trust him

-Maybe I will never be able to trust him again, even if he is telling the truth now

Rory sighed. As much as she liked to trust in her system, the pro/con list wasn’t exactly helping. She needed to sit with it, maybe add to it over the next few days, mull it over. She’d thought that talking it over would have helped, but, it turned out, that just lead to her making terrible decisions with ex-boyfriends.

Okay, so apparently she was thinking about this, now. She got up to get herself a second cup of coffee.

If she was being honest with herself, she didn’t understand what had happened last night. It seemed, in some sense, like a dream she’d have had, rather than something that would actually happen. Not that she dreamed about Jess. Much.

They’d met up as friends, right? They’d had a truce, and they’d agreed to meet up, and, yes, maybe there had been just a hint of flirting, but nothing overt, nothing that had lead her to think anything would happen. But the whole time they’d been there, he’d been acting…not exactly friend-like. 

It was probably just a nostalgia thing for him, she thought. And he’d always hated it in Stars Hollow; he was probably just miserable here and having Rory around was just a distraction from the town stuff that he’d always hated and the wedding stuff that he had to hate just as much. He was probably just bored, and she was there, and he’d kissed her on a whim, and it probably didn’t even mean anything to him, and there really wasn’t any point in analyzing it to death, and she probably wouldn’t be, if she was someone else.

But she wasn’t someone else, and so she couldn’t help but wonder, if it really had just been a whim, or boredom, or nostalgia, why Luke had said what he’d said to him yesterday about starting things back with her, or why he’d implied—or seemed to imply—maybe—

Nothing. He hadn’t implied anything; she was reading too much into a talk between old friends and exes that had gotten a little out of hand. He’d barely kissed her, after all. 

At first, until she’d kissed him back. She stirred her coffee idly, remembering how it’d felt to be held by him, how it felt to kiss him now, years later, and how his hands had felt in her hair—

“Morning, daughter! You were out late last night, huh? Get lucky?”

Rory jerked upright, staring at Lorelai in stunned silence for a second before realizing that no, Lorelai had not inherited the Gilmore mind-reading gift and had no idea she’d been fantasizing about kissing Jess just now, or that she’d actually been kissing him last night, and that she was kidding.

“Oh, yeah,” she replied. “Would have made Miss Patty proud.”

“That’s my girl,” Lorelai said, reaching for some coffee of her own. “You’re up early, huh?”

“I’m on the Grandma schedule now, apparently.”

“And you were up so late working, too. You must be exhausted, hon. Why don’t you take a nap or something? Go back to bed, be lazy.”

“I’m good, honestly,” Rory said. “We reporters don’t really sleep, anyways. Or eat. We just survive on coffee, whiskey, and the president’s tears.”

“Now that’s a diet I could get behind,” said Lorelai. “But seriously, I don’t want to have to put you to work all week if you’re exhausted.”

“Nope, I’m here, I’m ready to help.” Rory grinned at Lorelai, hoping her smile looked genuine rather than strained. 

“Okay, good, because I’m not going to lie to you, I’m really going to need it. Particularly in light of the recent phone conversation I just had with your grandmother.”

Uh-oh. Lorelai referring to Emily as Rory’s grandmother rather than her mother was never a good sign.

“What did Grandma say?”

“She called to invite us to Tuesday night dinner.”

“Tuesday night dinner? There is no Tuesday night dinner.”

“Not according to Emily Gilmore. Tuesday is the new Friday, didn’t you hear?”

Rory paused to think. “It’ll be nice, having dinner with Grandma, but why tonight, if she’s going to be helping with wedding stuff all week?”

“Apparently, she’s not going to be as free as she thought to help with the planning stuff, so she wants to see us beforehand, and get us to herself before more people start showing up for wedding festivities.”

“Makes sense,” said Rory, relieved at the fact that she wouldn’t be subjected to Emily’s Logan-related interrogations the entire week. It gave her a few days to come up with a reason he wouldn’t be at the wedding. (Unless the pro/con list took a drastic turn and she forgave him by then? Which it wouldn’t, there was no way. But if that was the case, why couldn't she just end things with him, and get it over with? Her head hurt.)

“It does not make sense! Now we’re having dinner with my mother tonight instead of ordering half the menu from Al’s Pancake World, which was my initial plan for our evening.”

“Yes, but I’m here, happy to act as a buffer if things get messy, and if dinner is gross, we can just order Al’s after.”

“That may be true, but you’re going to have a lot of buffering to do, my friend.”

“I’ll say,” said Luke, walking into the kitchen. “I think she’s still holding out hope you’ll call the wedding off and leave me at the altar.”

"That's not true," said Lorelai. "She's really come around on you. I'm pretty sure she likes you better than me now."

“You’re coming to Tuesday night dinner too, Luke?” Rory asked.

“Your grandmother insisted that we all be there, because Tuesday night dinner is for family,” said Lorelai.

“Tuesday night dinner didn’t exist a day ago,” Rory pointed out.

“Has that ever stopped your grandmother?”

“I’m going to need to borrow something to wear," said Rory, realizing that despite the fact that she'd packed the essentials, the essentials in this case consisted of jeans, her bridesmaid dress, and her outfit for the bachelorette party, which were far from options for a formal Gilmore dinner.

“Aw, man,” said Luke. “I forgot we have to dress up for this thing. I’ll have to tell Jess.”

“What?” said Rory, a little too loudly, twisting to face Luke. Her elbow knocked against her coffee mug, which promptly shattered on the floor.


	11. In Which Rory Gets Ready for Tuesday Night Dinner

**Summary for the Chapter:**

> Tuesday night dinner is already causing drama, and it hasn't even started yet.

**Notes for the Chapter:**

> I’m so sorry it’s taken me so long to update, and thank you so much to anyone who’s been reading and/or commenting to encourage me to continue with this. Things have been crazy and I got a bit off-track in terms of updating, but don't worry, I’m still fully intending to see the story through! (and there’s still a LOT that still needs to happen…) Hope you like this new chapter, and I hope to be more regular with updates going forward!

Rory leapt up and starting cleaning up her broken mug, but Luke grabbed a broom and dustpan and waved her away, telling her she’d cut her hands if she tried picking it up like that.

Lorelai acknowledged her erratic behavior, but luckily seemed to attribute a different motive to it. “Yep,” she said. “It’s going to be a super fun night. Me, you, your grandmother, Luke, and Jess for Tuesday night dinner. I don’t blame you for freaking out; it’s going to be interesting seeing what Emily Gilmore thinks of Jess.”

“She’s already met him,” Rory said automatically. Her head was stuck in the past too much this trip, and she couldn’t seem to get it out. 

“What? When?” demanded Lorelai. “Don’t tell me, he joined the Historical Society. No, the Chilton Boosters. No, I’ve got it. She finally ran out of women to hire in the entire state of Connecticut, so Jess is her new maid!”

“No, I, um, brought him to dinner with Grandma once. When we were dating,” Rory clarified. “It didn’t exactly go well.”

“I totally forgot about that,” Lorelai said. “God, it feels like that was so long ago, doesn’t it?”

“Yes,” said Rory emphatically. The past was in the past. She needed to stop thinking about Jess, and especially in the context of their past relationship. 

“What happened?” Lorelai asked.

“What?” Rory asked, having lost her train of thought again. Dammit, she needed so much more coffee.

“What happened when you brought Jess to dinner the last time? I remember her calling me later and freaking out, but I forgot exactly what prompted it. There was something that happened, maybe with Dean?”

“He showed up with a black eye,” said Rory. “And I got really upset because he wouldn’t say how he got it, so I thought he had a fight with Dean. Turns out he didn’t, though.” She shrugged. “Wait, I remember Grandma was actually really nice about it. She freaked out on you later?”

“Uh, yeah. You really think Emily Gilmore would just let that slide?”

“I guess not,” said Rory. It had actually been a nice memory with her grandmother, how sweet she’d been to Rory through the entire thing, letting her stay the night. She’d been naïve to think there wasn’t anything else to it, and it made her wonder what else she’d missed when she was younger, what other conversations that went over her head. It wasn’t a nice feeling. “Anyways, Luke,” Rory was going to try to be normal about this, particularly since she had a feeling Luke might be a little suspicious after the coffee-spilling incident, “I’m surprised Jess wanted to come tonight.”

“Well, he didn’t, but Emily kept insisting that I bring my family, and I figured that bringing Jess would be better than bringing Liz and T.J.”

“Yes,” said Rory and Lorelai simultaneously.

“Anyways, hon, I’m going to go get that stuff to finish the centerpieces, you make another pot of coffee, and we can reconvene to knock some wedding tasks off the list before the Gilmore dinner bonanza tonight,” said Lorelai, leaving Luke and Rory alone in the kitchen. Rory went to the coffeepot, but Luke stopped her. 

“I got it,” he said.

“Thanks,” she told him. “So, excited for the big day?”

Luke chuckled. “Yeah, I am. I’m not really the kind of guy that likes big parties, but your mom is determined to change my mind on that, and I think it’s actually working. Plus,” he paused, shaking the appropriately excessive amount of coffee into the filter, “The important thing is that I get to be with your mom. I’d do anything for that, even go through a crazy Stars Hollow wedding.”

“That’s really sweet, Luke,” she said. “I have to say, even though you’re already part of the family, I’m so happy for you and mom.”

“Thanks, Rory,” Luke said. “Uh, are you doing okay?”

“What? Of course!” said Rory, trying to utilize every ounce of caffeine she’d consumed to convey her general okay-ness. 

“Are you sure? Because you seem kind of…” he trailed off, and Rory had forgotten how perceptive he could be sometimes, even if he always played it off like he was too manly for emotions. “I mean, did Jess…say something to you? Because I can talk to him, I mean, I can see how it could be awkward when the two of you used to, you know, date, and now Lorelai and I are getting married.”

“Oh, no, not at all,” said Rory, a little too quickly and a little too emphatically, but definitely more in control. “He didn’t say anything. Everything’s good. I promise.” She just wanted the conversation to be over, because the idea that Jess would be blamed for her current weirdness was not only unfair, but would only result in making her feel more guilty and, consequently, act even weirder.

“Okay,” said Luke. “But you can talk to me if he’s bugging you, all right?”

“Thanks, Luke, but it’s all been fine.” Making a face, she changed the subject. “I just hope that dinner tonight goes okay.” Famous last words, she thought to herself. 

Hours later, Rory found herself standing in her bedroom in nothing but her jeans and a bra, staring at the clothes she’d laid out on her old bed, which consisted of every single article of clothing she’d brought with her from Boston. None of which was even close to correct for dinner at the Gilmore’s.

She was an adult now, for God’s sake. She could show up in jeans and a sweater and deal with the consequences. She wasn’t afraid of Emily Gilmore.

Who was she kidding? Of course she was.

Rory took a deep breath, threw her sweater back on, and resigned herself to borrowing something from Lorelai. Normally she wouldn’t hesitate, and Lorelai had already told her to go ahead and raid her closet, but Lorelai and Luke had seemed like they were in the middle of a conversation and Rory, consistent with her policy of not causing any problems and creating the most low-stress environment possible for Wedding Week, was trying to give them space. So she’d dawdled, curling her auburn hair with more care than she usually did, even attempting a halfway decent smoky eye. She was just stalling for time, she told herself, experimenting with wedding makeup, giving Luke and Lorelai space. She absolutely was not trying to make herself look nice for when she inevitably saw Jess tonight. That had nothing to do with it.

She was such a bad liar.

“Rory!” she heard Lorelai yell from upstairs. Finally.

She emerged from her old bedroom just as Lorelai bounded down the stairs. 

“Hurry! Take anything you want from my closet! We’re going to be late!”

“No we’re not!” Rory said. She’d timed everything right, and she’d been going to quietly call up to Lorelai in exactly three minutes if they still hadn’t emerged by then, and then that would still leave her fifteen minutes to find an outfit before they had to leave. At least.

“Yes we are! It’s almost 6:15!”

“What!” Rory yelped, grabbing her phone. No. It couldn’t be. She was sure she’d timed it right, not wanting to let lateness inject conflict into the evening so quickly—but Lorelai was right, her buffer was gone, and she needed to hurry.

She raced up the stairs into her mom’s bedroom, narrowly avoiding crashing into Luke on the way, and stared in paralyzed panic at the gigantic closet. What could she wear that would be suitable for tonight, or at least wouldn’t somehow offend her grandmother?

A dress. Dresses were easy, she wouldn’t have to deal with the complication of finding both a skirt and a top that matched, and she just needed to find one formal enough. She stared in paralyzed indecision, her mind for some reason refusing to do something as simple as pick a dress. It was a panicked, trapped feeling, one she recognized all too well from frequent nightmares about lateness and unpreparedness, and which she routinely overcompensated for by extremely earliness and over-preparation. Because when she really was running late she never knew what to do with herself, and right now the stress of running late was compounded by everything else she was frantically trying to suppress, and seriously, all she had to do was pick a dress, this really shouldn’t be that hard.

“Rory!” Lorelai called. “If we don’t leave now it’s going to cut into cocktail hour, and you know as well as I do that’s the most important part of dinner with the Gilmores!”

Shit. “You guys go ahead!” she called. “I’ll just be a second, I don’t want you to be late!”

She heard the door open downstairs, and voices too low to make out but that, unmistakably, no longer belonged to just Luke and Lorelai. 

She knew what was about to happen a second before it did. No, no, no—

“Okay, Luke and I are going to go, and then you can drive up with Jess as soon as you’re ready!”

No. No. No. Why couldn’t she just pick a dress? Or read a clock? Or interact normally with her ex-boyfriends? Or not fall for evil schemes concocted by the family of her maybe-current boyfriend?

Too far down the rabbit hole, Gilmore, she told herself. One problem at a time. 

Mustering up her cheeriest voice, she called down to her mom. “No, that’s okay! Jess can go with you guys! I’ll be ready in a sec, I’ll just drive myself!”

“Jess says it’s fine, he’ll drive you,” her mom called back up. Rory highly doubted that.

“Besides, Rory, it might be better that, uh, we get some time with your grandma before Jess gets there,” said Luke, in a tone that was clearly striving for diplomatic.

“Yes, we don’t want Emily Gilmore getting too excited and starting to look for a second husband!” Lorelai quipped, and Rory shuddered. Speaking of nightmares, she now knew what hers would feature tonight.

“Mom, seriously, I can drive!” she called, her voice less cheerful and approaching frantic.

“We’ll see you in a few, hon!” Lorelai called. “And I do mean a few, because please don’t leave me alone for that long with Grandma! Bye!”

And the front door slammed shut, leaving Rory not only frozen, but trapped. The silence from downstairs, she thought, probably indicated that Jess was about as excited to see her again as she was to see him. Probably much less, to be fair.

She sighed, staring again at the closet. On the upside, the dress-picking panic-indecisiveness suddenly seemed much less daunting compared to the prospect of a car ride to Hartford seated next to the ex-boyfriend she’d kissed last night. Strangely, Rory often dealt with stress this way—by discovering something way more stressful to fixate on, she was able to then think her way through her initial problem. Was it healthy? Probably not. Did it work? Kind of.

She could do this. No fake fur. No feathers. No neon. Black. Black was safe, and dressy, and if she decided to reenact her spill extravaganza from this morning, it wouldn’t stain. She grabbed the first black dress she saw and shoved it on, giving herself no time to second-guess her decision. The sooner she left this room, the sooner she could get to her grandmother’s house and the ride with Jess would be over and done with. 

She smoothed the silky fabric, which was more comfortable than she’d expected, and glanced at herself in the mirror on her way to the door. When she saw her reflection, she froze. The black dress wasn’t too short, and it had three-quarter-length sleeves, but its wrap style emphasized the curve of her waist, and its V-neck came down a bit lower than she’d normally have chosen for herself. Her hand rose, unbidden, to her curled hair, as she saw what the combination of her procrastination-primping and last-minute dress added up to. She looked…sexy.

Sexy wasn’t a word Rory generally used to describe herself. Ever, in fact. It also wasn’t a word anyone else would ever use in conjunction with her; she didn’t think she’d ever even heard Logan say it. Pretty, sure. Beautiful, maybe. But not sexy. Not Rory. 

It wasn’t like the dress was even that scandalous, or the hair, or the makeup. But all together, it was…well. It wasn’t what she would normally choose to wear to a dinner that included her grandmother and a guy she was trying to avoid kissing again.

She should take it off, find something else. Jess would think…she didn’t know what Jess would think, but he might get the wrong impression. Not that she knew what the wrong impression was, not really, since she wasn’t sure what the right one was, either, but she had the distinct impression that it wasn’t going to be helped by looking…well, better than she’d looked in awhile, if she were being honest. She admired the dress in the mirror for just a moment longer. Maybe it wouldn’t be so wrong? If it made her feel good, what was the harm in feeling, well, sexy, for once in her life?

“Rory?” Jess’s voice called up the stairs, tentatively. “Are you okay?”

How long had she been staring at herself in a mirror for? 

“I’m fine!” she yelled, definitely louder than she needed to. “I’ll be there in a minute!”

“Look, if you really don’t want to drive with me, or if you really don’t want me to go tonight, I get it,” he said, clearly not buying it. He also wasn’t yelling, which meant that he must be right outside the door. How had he gotten upstairs without her noticing? She was really off her game today, and she needed to get in the zone if she was going to get through Tuesday night dinner. “I can just tell Luke I wasn’t feeling well, or that someone at Truncheon had an emergency and I had to get on a call.”

No. No more drama on her account. No more lying to her mom and Luke than was absolutely necessary. Like about her job, apartment, or relationship status. She needed to stop him in his tracks, and that, unfortunately, left her no time to change again. She drew in a deep breath and yanked the door open.

Jess was leaning against the doorframe, staring at his feet, but his eyes jerked up to hers when she opened the door. She saw his expression rapidly go from resigned to, well. Something that was definitely not disinterest, she thought, judging by the heat flaring in his gaze. 

She swallowed. “No.”

He seemed to have lost track of the conversation. “No what?” He was looking at her like he’d forgotten what had happened last night. Like he was much more interested in what was happening right now, and there was a part of her that was way too glad she hadn’t had time to change out of the dress.

“No,” she repeated, firmly. “I mean, yes.” She wasn’t making sense either, and she needed to get a handle on this. “You should come to dinner.”

She felt his gaze recede a bit, becoming less easy to read. It was for the best, she told herself. 

“Are you sure?” he asked.

She nodded. “Yes. It’s what Luke wants. You should come. We can go together. It’s not a big deal.”

The instant the last sentence was out of her mouth, she regretted it, and almost flinched when his eyes went dark, becoming impenetrable again.

“Right,” he said, and his tone had more of a bite to it than it had a moment ago. “Not a big deal.” 

And he turned and went down the stairs, presumably expecting her to follow him.


End file.
